Two step process of the manufacture of carbohydrate composition

Abstract

The technology disclosed in this specification relates to carbohydrate composition comprising a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and having a defined ratio of a sum of the 1,6 and the 1,4 linages to the 1,3. The composition made in process comprising mixing a solution comprising glucose syrup with acid and heating the solution to evaporate a portion of the liquid and then decreasing the pressure on the mixture to obtain the carbohydrate composition. The compositions can be used in conjunction with high potency sweeteners to replace nutritive sweeteners to replace for example to replace lost bulk. Also, the composition can be used to provide dietary fiber to edible compositions or are used as bulking agents.

Description

TWO STEP PROCESS OF THE MANUFACTURE OF CARBOHYDRATE COMPOSITION

[0001] Disclosed herein are processes for making carbohydrate compositions. More specifically, the carbohydrate compositions are digestion resistant or slowly digestible short chain glucose polymers.

[0002] Compositions substantially comprising short chain carbohydrate polymers are useful for various purposes and are made by various processes. Such compositions may be called soluble fiber or resistant maltodextrin, or dextrin. Frequently, they are digestion resistant or slowly digestible. They can be used in conjunction with high potency sweeteners to replace nutritive sweeteners to replace. Often, they provide dietary fiber to edible compositions or are used as bulking agents. Some of these compositions are molecules that are non-glucose polymers or are molecules combining glucose with other sugars or polyols. Others are polymers of glucose.

[0003] Among the examples of glucose polymers some are made using enzymes that catalyze hydrolysis and polymerization of glucose oligosaccharides. Other processes use heat and acid in place of enzymes to catalyze the reaction. For example, United States Patent Number 7,608,436 describes a process comprising heating an aqueous feed composition of monosaccharide or saccharide oligomers in the presence of a catalyst that accelerates the cleavage and reformation of glucosyl bonds to create preferentially non-linear oligosaccharides. United States Publication Number 2016-015065 is another example process using heat and acid. It describes a process that heats a feed composition comprising greater than 90% glucose and a catalyst to form a defined composition. A third example is United States Patent Number 9,783,619, which describes a process comprising preparing a dehydrated acidified starch and treating the dehydrated acidified starch in a thin-layer reactor at high temperature.

[0004] The processes using heat and acid, avoid the expense and complication of enzymatic processes but rely on a less controlled equilibrium of hydrolysis and polymerization reactions. So fractionization is commonly used to obtain a desired product. The technology disclosed in this specification improves on the prior art disclosing a two-step process to more controllably from a carbohydrate composition.BRIEF DESCRIPTION OF THE FIGURES

[0005] The technology described in this specification can be better understood with reference to the figures, which are provided for illustrative purposes and are not intended to limit the full scope of the technology described.

[0006] Figure 1 is a graph comparing the distribution of glucose oligosaccharides in an illustrative intermediate carbohydrate composition to 42DE and 63DE glucose syrups.

[0007] In one aspect, this specification describes digestion resistant or slowly digestible oligosaccharides, which collectively are called in this specification a carbohydrate composition. Embodiments carbohydrate compositions have structure described as follows. In any embodiment, this specification describes a carbohydrate composition comprising a plurality of glucose polymer comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages wherein the weight percentage of the 1,6 linkages is in an amount greater than 20% (wt.%) of the composition. In any embodiment, this specification describes a carbohydrate composition comprising a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to the 1,3 is at least 4.9 or at least 5, or greater than 5 or from 4.9, or from 5.0, or from 5.1 to 10, or from or from 4.9, or from 5.0, or from 5.1 to 9, or from 4.9, or from 5.0, or to 8, or from 4.9, or from 5.0, or to 7.5. In any embodiment this specification describes a carbohydrate composition comprising a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and a total dietary fiber content greater than about 60%, or greater than about 70% wherein the weight percentage of the 1,6 linkages is in an amount greater than 20% (wt.%) of the composition, and wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to 1,3 linkages is greater than 5. The plurality of glucose polymers are essentially polymers only comprising glucose residues, and in embodiments comprise greater than 90% glucose residues, greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues. Here glucose residues refers to the subunits of the polymer, which are polymerized glucose units. In any embodiment the composition consists essentially of glucose polymers or consists of glucose polymers. Additionally in any embodiment the composition comprises, consists, or consists essentially of glucose polymers having one or more or all of the properties described in this paragraph.

[0008] In any embodiment, in any embodiment, this specification describes a carbohydrate composition wherein the weight percentage of the 1,6 linkages is from 20% to about 50%, or20% to about 45%, or from 20% to about 40%, or from 20% to about 35%, or from 20% to about 30%.

[0009] In any embodiment, this specification describes a carbohydrate composition wherein the weight percentage of the 1,6 linkages is from 20% to about 30% or from about 20% to about 29%, or to about 28%, or to about 27%, or to about 26%, or to about 25%. In another embodiment, this specification describes a carbohydrate composition wherein the weight percentage of the 1,6 linkages is in an amount from about 21% to about 30%, or from about 22% to about 30%, or from about 23% to about 30%, or from about 23% to about 30% or to about 24% to about 30%. In any embodiment, this specification describes a carbohydrate composition wherein the weight percentage of the 1,6 linkages are in amount from about 22% to about 28% or from about 23% to about 27%, or from about 24% to about 26%.

[0010] In any embodiment, this specification describes a carbohydrate composition wherein the (1,6 +1,4) to 1,3 linkages is from 5 to about 30 or from 5 to about 25 or from 5 to about 20 from 5 to about 15.

[0011] In any embodiment, this specification describes a carbohydrate composition wherein the (1,6 +1,4) to 1,3 linkages is from 5 to about 10, or from about 6 to about 10. In any embodiment, this specification describes a carbohydrate composition wherein the (1,6 +1 ,4) to 1,3 linkages is from 5 to about 10 or from 5 to about 9 or from 5 to about 8. In any embodiment, this specification describes a carbohydrate composition wherein the (1,6 +1,4) to 1,3 linkages is about 6 to about 9 or from about 6 to about 8.

[0012] In any embodiment, this specification describes a carbohydrate composition wherein a ratio of 1,6 to 1,3 linkages greater than about 3 or greater than about 4, or greater than about 5.

[0013] In any embodiment, this specification describes a carbohydrate composition wherein the ratio of 1,6 to 1,3 linkages is from about 3 to about 15 or about 10, or from about 4 to about 15 or about 10, or from 5 to about 15 or about 10.

[0014] In any embodiment, this specification describes a carbohydrate composition wherein the ratio of 1,6 / 1, 3 linkages is from about 3 to about 7 or from about 3 to about 6. In any embodiment, this specification describes a carbohydrate composition wherein the ratio of 1,6 to 1,3 linkages is from to about 4 to about 7 or from about 4 to about 6. In any embodiment,this specification describes a carbohydrate composition wherein the ratio of 1,6 to 1,3 linkages is from to about 4.5 to about 7 or from about 4.5 to about 6.

[0015] In any embodiment, this specification describes a carbohydrate composition wherein the ratio of 1,6 to 1,3 linkages is from about 5 to about 10, or is from greater than 5 to about 10, or is from about 5.25 to about 10, or is from about 5.25 to about 9, or from about 5.25 to about 8, or from about 5.25 to about 7, or from about 5.25 to about 6.

[0016] In any embodiment, this specification describes a carbohydrate composition wherein a ratio of 1,6 to 1,4 linkages from greater than about 3 or greater than about 4, or from about 3 to about 6, or from about 3 to about 5. In any embodiment, this specification describes a carbohydrate composition wherein a ratio of 1,6 to 1,4 linkages is greater than 4.1, or from 4.1 to 10, or from 4.1 to 9, or from 4.1 to 8, or from 4.1 to 7, from 4.1 to about 6 or from 4.1 to about 5.

[0017] In any embodiment, this specification describes a carbohydrate composition wherein a ratio of l,4to 1 / 2 linkages less than about 1, or less than 1, or less than 0.95. In any embodiment, this specification describes a carbohydrate composition wherein a ratio of 1 ,4 / 1 / 2 linkages from 0.10 to 0.95, or from 0.20 to 0.95, or from 0.30 to 0.95, or from 0.40 to 0.95, or from 0.50 to 0.95 or from 0.60 to 0.95 or from 0.70 to 0.95.

[0018] In any embodiment, this specification describes a carbohydrate composition wherein a sum of 1,6 + 1,4 linkages greater than about 28%, or greater than about 29%, or greater than about 30%.

[0019] In any embodiment, this specification discloses a carbohydrate composition wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to 1,3 linkages is greater than 3, or greater than 4, or greater than 5. In any embodiment, this specification discloses a carbohydrate composition the (1,6 +1,4) to 1,3 ration is from 4 to 6, or from 5 to 6.[00201 In any embodiment, this specification describes a carbohydrate composition wherein the percentage of 1,6 linkages is greater than the percentage 1,2 linkages.

[0021] In any embodiment, this specification describes a carbohydrate composition wherein the percentage of 1,6 linkages is greater than the percentage of 1,4 linages.

[0022] In any embodiment, this specification describes a carbohydrate composition wherein the percentage of 1 ,6 linkages is greater than the percentage of 1 ,2 linkages, and the percentageof 1,6 linkages is greater than the percentage of 1,4 linkages, and the percentage of 1,2 linkages is greater than the percentage of 1,4 linkages.

[0023] In any embodiment, this specification describes a carbohydrate composition wherein a weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 (“DP3 to DP5”) is greater than about 25%, or greater than about 30%, or greater than about 35%, or greater than about 40%. In any embodiment, this specification describes a carbohydrate composition wherein the DP3 to DP5 is from about 25% to about 40%, or from about 25% to about 35%. In any embodiment, this specification describes a carbohydrate composition wherein the DP3 to DP5 is from about 26% to about 35%, or from about 27% to about 35%, or from about 28% to about 35%. In any embodiment, this specification describes a carbohydrate composition wherein the DP3 to DP5 is from about 28% to about 34%, or from about 28% to about 33%, or from about 28% to about 32%.

[0024] In any embodiment, this specification describes a carbohydrate composition or intermediate composition wherein a weight percentage of glucose polymers having a degree of polymerization greater than 6 (“DP6+”) is less than 50%, or less than 45%, or from about 40% to about 50%, from about 40% to about 45%. In any embodiment, this specification describes a carbohydrate composition or intermediated composition wherein a ratio of the weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 to weight percentage of glucose polymers having a degree of polymerization greater than 6 (“DP3 to DP5 / DP6+”) is greater than about 0.5, or from about 0.5 to about 2.0, or from about 0.5 to about 1.5, or from about 0.5 to about 1.0.

[0025] In any embodiment, this specification discloses an intermediate carbohydrate composition wherein the DP6+ content is from about 6% to about 15% or from about 7% to about 15%, or from about 8% to about 15%, or from about 9% to about 15%, or from about 10% to about 15%. In any embodiment, this specification discloses a carbohydrate composition wherein the DP6+ content is from about 5% to about 14%, or from about 5% to about 13% or from about 5% to about 12% or from about 5% to about 11%. In any embodiment or an intermediate carbohydrate composition the DP6+ content is from about 5% to about 12% or from about 7% to about 12% or from 8% to about 12% or from about 9% to about 12%.

[0026] In any embodiment, this specification discloses a carbohydrate composition a weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 (“DP3 to DP5”) is greater than about 25%, or greater than about 30%, or greater than about 35%, orgreater than about 40%. In any embodiment, this specification discloses a carbohydrate composition the DP3 to DP5 is from about 25% to about 40%, or from about 25% to about 35%. In any embodiment, this specification discloses a carbohydrate composition the DP3 to DP5 is from about 26% to about 35%, or from about 27% to about 35%, or from about 28% to about 35%. In any embodiment, this specification discloses a carbohydrate composition wherein the DP3 to DP5 is from about 28% to about 34%, or from about 28% to about 33%, or from about 28% to about 32%.

[0027] In any embodiment described in this specification, a carbohydrate composition has total dietary fiber content greater than about 60%, or greater than about 70%, or greater than about 80% or from about 60% to about 90% or from about 70% to about 90% or from about 70% to about 80%.

[0028] In another aspect this specification describes intermediate carbohydrate compositions useful for making a final carbohydrate composition. In some respects the intermediate carbohydrate compositions are like the carbohydrate compositions described above. For examples, the intermediate carbohydrate compositions are carbohydrate compositions comprising a plurality of glucose polymers having a mixture of 1-2, 1 -3 , 1-4, and 1 -6 linkages. A key difference, however, is that the intermediate carbohydrate compositions have a low degree of polymerization, as illustrate by having relatively few oligosaccharides having degree of polymerization of 6 or more. In any embodiment, this specification discloses an intermediate carbohydrate composition comprising a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages wherein the weight percentage content of the glucose polymers having a degree of polymerization greater than 6 (“DP6+”) is less them about 25% or less than 20% or less than about 15%, or from about 1% or from about 3% or from about 5% to about 25%, or from aboutl%, or from about 3%, or from about 5% to about 20%, or from about 1% or from about 3% or from about 5% to about 15%.

[0029] In any embodiment, this specification discloses an intermediated composition useful for making a final carbohydrate composition wherein a ratio of glucose polymers having a degree of polymerization in the range from DP3 to DP5 to the glucose polymers having a degree of polymerization DP6+ (“(DP3 to DP5) / DP3”) is greater than about 2.0 or greater than 3.0, or from about 2.0 to 5.0 or from about 2.0 to 4.0.

[0030] In any embodiment, this specification discloses a carbohydrate composition wherein a ratio of glucose polymers having a degree of polymerization in the range from DP3 to DP5to the glucose polymers having a degree of polymerization DP6+ (“(DP3 to DP5) / DP3”) is greater than about 2.0 or greater than 3.0, or from about 2.0 to 5.0 or from about 2.0 to 4.0.

[0031] In one aspect this specification describes methods for making carbohydrate compositions. In any embodiment, this specification describes a two-step processing for making a carbohydrate composition, for example as described above. In any embodiment described in this specification a first step of a two-step process to make a carbohydrate composition comprises heating and evaporating a mixture of glucose syrup and acid at near atmospheric pressure and a relatively low temperature until the dry solids content of the mixture increases by at least about 10%. This first step takes a relatively long time and makes an intermediate carbohydrate composition comprising a plurality of short chain glucose oligosaccharides having diverse linkages. In a second step, a two-step process to make a carbohydrate composition comprises decreasing the pressure in the reaction vessel to near vacuum conditions to obtain a dry powder. This second step takes a relative short time and makes glucose oligosaccharides substantially retaining the linkage structure of the intermediate carbohydrate composition but that having a higher degree of polymerization.

[0032] Varying the reaction conditions of the first step or the second step can alter the structure of the carbohydrate composition. Regarding the first step, one can adjust the reaction by reducing or increasing temperature, or by increasing or reducing evaporation time. This changes the mixture of linkages among glucose units in the intermediate carbohydrate composition, and thereby changes the linkages among glucose units in the carbohydrate composition. Regarding the second step, by increasing or decreasing the evaporation time, the degree of polymerization of the carbohydrate composition can be adjusted.

[0033] Various other embodiments of a method for making a carbohydrate composition follow. In any embodiment, this specification describes a method of making a carbohydrate composition comprising: a) mixing a solution comprising a glucose syrup having a dry solids content of at least about 50%, or at least about 60% or at least about 70%, or at least about 80% dry solids or from about 60% to about 90% or from about 70% to about 90% or from about 70% to about 80% with acid wherein the acid is in an amount from about 0.01% to 0.1 % by weight of the solution b) heating the solution to evaporate a portion of the liquid in the glucose syrup to increase solids content of the syrup by percentage (wt.%) of at least about 10% or at least about 20% or least about 30% or at least about 40% at a pressure from about 0.75 bar to about 1.50 bar, or about 0.8 bar to about 1.2 bar, or from about 0.9 to about 1.1 bar to obtainan intermediate carbohydrate; c) decreasing the pressure on the mixture to less than 0.25 bar, or less than 0.10 bar, or less than 0.05 bar or from 0.01 bar to 0.25 or 0.01 bar to 0.10 bar or from 0.01 bar to 0.05 bar for a time less than 10 minutes, or less than 5 minutes, or less than 1 minute to obtain the carbohydrate composition.10034] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the glucose syrup has from about 65% to about 75% dry solids.

[0035] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the glucose syrup has DE greater than about 60DE or greater than about 80DE or greater than about 90DE, wherein, preferably, the DE is at greater than about 80DE, or greater than about 90DE.

[0036] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the acid is selected from the group consisting of hydrochloric acid, sulfuric acid. Other useful acids include but are not limited to, adipic acid, acetic acid, citric acid, fumaric acid, gluconic acid, lactic acid, maleic acid, malic acid, succinic acid, tartaric acids, sulfurous acid, thiosulfuric acid, dithionic acid, pyrosulfuric acid, selenic acid, selenious acid, nitric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, boric acid, perchloric acid, hypochlorous acid, hydrobromic acid, and mixture thereof.

[0037] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the acid is in an amount from about 0.01% to about 0.09%, or from about 0.01% to about 0.08%, or from about 0.01% to about 0.07%, of the solution, or from about 0.02% to about 0.1% or from about 0.03% to about 0.1% or from about 0.02% to about 0.08%, or from about 0.03% to about 0.07%.

[0038] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the pH of the mixture is less than 2.0, or is less than 1.0, or from 0.1 to 2.0, or 0.1 to 1.0.

[0039] In any embodiment, this specification describes a method of making a carbohydrate composition wherein during the heating the solution of step b) is for a time from about greater than 1 hour or from about 1 hour to about 5 hours, or from about 1 to about 4 hours or from about 1 to about 3 hours or from about 1.5 hour to a 2.5 hours.

[0040] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the intermediate carbohydrate composition has a dry solids content offrom 60%, or from 70%, or from 80% to 99%. In any embodiment, this specification describes a method of making a carbohydrate composition wherein the intermediate carbohydrate composition has a dry solids content from 81% to 95% or from 82% to 95%, or from 83% to 95% or from 84% to 95%, or from 85% to 95%.

[0041] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the intermediate carbohydrate has a dextrose equivalent from about 5 ODE to about 70DE, or from about 55DE to about 65DE.

[0042] In any embodiment, this specification describes a method of making a carbohydrate composition wherein the during the decreasing pressure step the intermediate carbohydrate composition is heated to a temperature from about 100° C to 180° C.

[0043] Advantageously, the carbohydrate compositions described in this specification can be made to have at least about 70% (wt.%) total dietary fiber and obtain a desired degree of polymerization profile without using fractionation such as by chromatography. In any embodiment, this specification describes a method for making a carbohydrate composition (as described herein) that does not comprise fractionization, such as by chromatography, such by using simulated moving bed, or sequential simulated moving bed technologies.

[0044] Advantageously, the carbohydrate compositions described in this specification can be made without use of enzymes or enzymatic treatment. In any embodiment described in this specification a method for making a carbohydrate composition that does not comprise enzymes or enzymatic treatment.

[0045] Other steps to decolor or decolor the carbohydrate composition can also be used such as passing washing the carbohydrate composition in water, passing a carbohydrate composition through carbon filtration system or an ion exchange system.

[0046] The carbohydrate compositions described in this specification can be used in edible compositions to replace the bulk properties of sugar and eliminate or reduce the caloric content.

[0047] Additional embodiments according to the disclosure relate to edible compositions or products chosen from food or beverage products or nutritional supplements, said foodstuff or product comprising a carbohydrate composition comprising a carbohydrate composition as described above. Non-limiting examples of edible compositions include but are not limited cereals, bars (granola bars, snack bars, cold pressed bars), confectioneries, beverages, and savory products, fruit preparations used for fillings, pastries, pastries fillings. Such foodproducts can be made using formulations common in the art. Edible compositions may also be non-nutritive compositions such as tooth pastes or other ingestible hygienic compositions or may be non-active ingredients in pharmaceutical compositions, or may provide pre-biotic or pro-biotic effect or may be an non-active ingredient in a nutritional supplement.

[0048] In embodiments edible compositions comprise a carbohydrate composition, as described in this specification, and at least one other ingredient. The one other ingredient may be any ingredient commonly used in a edible composition. Non-limiting examples of the one other ingredient include starches (including high amylose and low amylose variants), proteins (from animal and plant sources), sweeteners (including nutritive, non-nutritive, and high potency sweeteners), gums, hydrocolloids, water, flavorings, seasoning, preservatives, leavening agents, coloring agents, flavors, fragrances, and essences.

[0049] In at least some embodiments an edible composition is a food compositions. Some embodiments of food compositions using the carbohydrate compositions described in this specification include bread, pastries, cookies, muffins, pizza doughs, baked goods, meats, alternative meat product; dry soup mixes, bakery mixes, frosting mixes, spice mixes and blends, coverage powders, condiments, gravy mixes, sauce mixes and frozen dairy foods, and fat mimetics.

[0050] The edible composition may be low or reduced calorie. In addition, the carbohydrate compositions described in this specification can be used more generally, whether in an edible composition or other type of composition, as a tableting compound, anti-caking agent, as a coating, as an agglomeration aid.10051] In at least some embodiments a carbohydrate composition is used in an edible composition to reduce caloric sweetener content like sucrose or fructose. In such embodiments the carbohydrate may be used in combination with a non-nutritive or high potency sweetener to to reduce the caloric sweetener by up to 100%, up to 90%, up to 80%, up to 75%, up to 70%, up to 60%, up to 50%, up to 40%, up to 30%, up to 25%, up to 20%, up to 15%, up to 10%, or up to 5% or from 1% to 100% or from 1% to 75% or from 1% to 67%, or from 1% to 60%, or from 1% to 50%, or from 1% to 40%, or from 1% to 33, or from 1% to 30%, or from 1% to 25%, or from 1% to 20%, or from 1% to 15%, or from 1% to 10%, or from 1% to 5%.

[0052] In at least some embodiments an edible composition comprises a carbohydrate composition in an amount from 1% to 50%, or to 45%, or to 40%, or to 35%, or to 30%, or to25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2%.

[0053] Within this specification the term “dextrose equivalent” (and abbreviate as “DE”) measures the amount of reducing sugars present in a sugar product expressed as a percentage on a dry basis relative to dextrose. For example, a product having a dextrose equivalent value 10 (or “DE 10”) has about 10% of the reducing power of dextrose. The dextrose equivalent also gives an indication of the average degree of polymerization (DP) for starch sugars. Dextrose equivalent is a well understood term in the art, and the provided definition is for illustrative purposes only and is not intended to limit the full understanding of the term. Dextrose equivalent can be measured by any method known in the art.

[0054] Within this specification glycosidic linkage analysis was done using partially methylated alditol acetates (PMAA) derivatization method for GC-MS. Samples (3 mg) were dissolved in 500 pl DMSO, 200 pl n-butyl lithium were added, and tubes were incubated for 40 minutes. Methyl iodide (300 pl) was added and stirred for 1 hour. The resulting mixtures were partitioned with deionized water and chloroform. The chloroform layer was separated and dried under a stream of nitrogen. Samples were hydrolyzed with 2M TFA for 1 hour at 121° C containing 1 mg / ml inositol as an internal standard. The samples were then dried under the stream of nitrogen. Dry samples were reduced with 100 pl of IM ammonium hydroxide with 20 mg / ml of sodium borodeuteride in DMSO for 90 minute at 40° C. The reaction was quenched with glacial acetic acid. Samples were O-acetylated with 100 pl of 1- methylimidazole and 500 pl of acetic anhydride. The resulting partially methylated alditol acetates were partitioned with deionized water and methylene chloride. The methylene chloride layer was separated and dried under a stream of nitrogen. Samples were dissolved in 1 ml acetone and analyzed by GC-MS (GC - Agilent 7890A equipped with FID detector, MS - Agilent 5975C, column SP-2330).

[0055] Within this specification carbohydrate (DP) distribution analysis was done as follows. Samples were prepared at 1% solids in HPLC grade water and analyzed on an Agilent 1260 HPLC-RID instrument. HPLC grade water was the mobile phase with a flow rate of 0.5 ml / minute using a Bio-Rad Aminex HPX-42A column for separation. Samples were reported in area percent.

[0056] Within this specification, total dietary fiber analysis was done as follows. Samples were prepared by adding one lg of sample per 40 ml of pancreatic alpha-amylase / AMGmixture to a 250mL Fisherbrand soda glass, wide mouth bottle. Bottles were shaken in a Grant OLS 200 shaking incubation bath at 37° C and 150 rpm in orbital motion for 16 hours. After 16 hours, removed all bottles and added 3.0 mL of 0.75 M Tris buffer solution to terminate the reaction. Slightly loosened the cap and placed in the water bath at temperature in the range from 95° to 100° C for 20 minutes. To bottle solution added 0.1 mL of protease solution and incubate at 60° C for 30 minutes. Adjusted pH to approximately 4.3 by adding 4.0 mL of 2 M acetic acid. With 1.0 mL ofD-sorbitol as internal standard. The total dietary fiber was analyzed by HPLC (Waters Sugar-Pak column with flow rate 0.5 mL / min) after deionization using mix of Amberlite FPA 53 (OH-) and Ambersep 200 (H+).

[0057] Use of “about” to modify a number is meant to include the number recited plus or minus 10%. Where legally permissible recitation of a value in a claim means about the value. Use of about in a claim or in the specification is not intended to limit the full scope of covered equivalents.

[0058] Recitation of the indefinite article “a” or the definite article “the” is meant to mean one or more unless the context clearly dictates otherwise.[0059| While certain embodiments have been illustrated and described, a person with ordinary skill in the art, after reading the foregoing specification, can effect changes, substitutions of equivalents and other types of alterations to the methods, and of the present technology. Each aspect and embodiment described above can also have included or incorporated therewith such variations or aspects as disclosed regarding any or all the other aspects and embodiments.10060] The present technology is also not to be limited in terms of the aspects described herein, which are intended as single illustrations of individual aspects of the present technology. Many modifications and variations of this present technology can be made without departing from its spirit and scope, as will be apparent to those skilled in the art. Functionally equivalent methods within the scope of the present technology, in addition to those enumerated herein, will be apparent to those skilled in the art from the foregoing descriptions. Such modifications and variations are intended to fall within the scope of the appended claims. It is to be understood that this present technology is not limited to methods, conjugates, reagents, compounds, compositions, labeled compounds or biological systems, which can, of course, vary. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. It is also to be understood thatthe terminology used herein is for the purpose of describing aspects only and is not intended to be limiting. Thus, it is intended that the specification be considered as exemplary only with the breadth, scope and spirit of the present technology indicated only by the appended claims, definitions therein and any equivalents thereof. No language in the specification should be construed as indicating any non-claimed element as essential.

[0061] The embodiments illustratively described herein may suitably be practiced in the absence of any element or elements, limitation or limitations, not specifically disclosed herein. Thus, for example, the terms “comprising,” “including,” “containing,” etc. shall be read expansively and without limitation. Additionally, the terms and expressions employed herein have been used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the claimed technology. Additionally, the phrase “consisting essentially of’ will be understood to include those elements specifically recited and those additional elements that do not materially affect the basic and novel characteristics of the claimed technology. The phrase “consisting of’ excludes any element not specified.

[0062] In addition, where features or aspects of the disclosure are described in terms of Markush groups, those skilled in the art will recognize that the disclosure is also thereby described in terms of any individual member or subgroup of members of the Markush group. Each of the narrower species and subgeneric groupings falling within the generic disclosure also form part of the technology. This includes the generic description of the technology with a proviso or negative limitation removing any subject matter from the genus, regardless of whether the excised material is specifically recited herein.

[0063] As will be understood by one skilled in the art, for any and all purposes, particularly in terms of providing a written description, all ranges disclosed herein also encompass any and all possible subranges and combinations of subranges thereof. Any listed range can be easily recognized as sufficiently describing and enabling the same range being broken down into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each range discussed herein can be readily broken down into a lower third, middle third and upper third, etc. As will also be understood by one skilled in the art all language such as “up to,” “at least,” “greater than,” “less than,” and the like, include the number recited and refer to ranges which can be subsequently broken down into subranges as discussed above. Finally, as will beunderstood by one skilled in the art, a range includes each individual member, and each separate value is incorporated into the specification as if it were individually recited herein.

[0064] The technology disclosed in this specification can be better understood with reference to the following aspects, which are not intended to limit the full scope of the disclosed technology.

[0065] 1. A carbohydrate composition comprising:

[0066] a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and[0067| wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to the 1,3 linkages is at least 4.9 or at least 5, or greater than 5 or from 4.9, or from 5.0, or from 5.1 to 10, or from or from 4.9, or from 5.0, or from 5.1 to 9, or from 4.9, or from 5.0, or to 8, or from 4.9, or from 5.0, or to 7.5;

[0068] wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues;

[0069] wherein, optionally, the composition consists essentially of the glucose polymers or consist of the glucose polymers.[0070| 2. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and

[0071] wherein a ratio of 1,6 to 1,3 linkages is greater than about 3 or greater than about 4, or greater than about 5

[0072] wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues;

[0073] wherein optionally the composition consists essentially of the glucose polymers or consist of the glucose polymers.

[0074] 3. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and

[0075] wherein a ratio of 1,6 to 1,4 linkages is greater than 4.1, or from 4.1 to10, or from 4.1 to 9, or from 4.1 to 8, or from 4.1 to 7, from 4.1 to about 6 or from 4.1 to about 5

[0076] wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues;

[0077] wherein optionally the composition consists essentially of the glucose polymers or consist of the glucose polymers.

[0078] 4. A carbohydrate composition comprising a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and

[0079] wherein a ratio of 1,4 to 1,2 is less than about 1, or less than 1, or less than 0.95[00801 wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues;

[0081] wherein optionally the composition consists essentially of the glucose polymers or consist of the glucose polymers.[00821 5. The carbohydrate composition of claims 1 and 2.

[0083] 6. The carbohydrate composition of claims 1 and 3.

[0084] 7. The carbohydrate composition of claims 1 and 4.

[0085] 8. The carbohydrate composition of claims 2 and 3.

[0086] 9. The carbohydrate composition of claims 2 and 4.

[0087] 10. The carbohydrate composition of claims 3 and 4.

[0088] 1 1 . The carbohydrate composition of claims 1 , 2, and 3.

[0089] 12. The carbohydrate composition of claims 1, 2, and 4.|0090] 13. The carbohydrate composition of claims 1, 3, and 4.

[0091] 14. The carbohydrate composition of claims 2, 3, and 4.

[0092] 15. The carbohydrate composition of claims 1, 2, 3, and 4.

[0093] 16. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and having one or more properties selected from the group consisting of

[0094] a) a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to the 1,3 linkages is greater than 5

[0095] b) a ratio of 1,6 to 1,3 linkages is greater than about 3 or greater than about 4, or greater than about 5

[0096] c) a ratio of 1,6 to 1,4 linkages is greater than 4.1, or from 4.1 to 10, or from 4.1 to 9, or from 4.1 to 8, or from 4.1 to 7, from 4.1 to about 6 or from 4.1 to about 5 and

[0097] d) a ratio of 1,4 to 1,2 is less than about 1, or less than 1, or less than0.95,

[0098] wherein, optionally, the composition consists essentially of the glucose polymers or consist of the glucose polymers.

[0099] 17. The carbohydrate composition of any preceding claim wherein the weight percentage of the 1,6 linkages in the composition are in an amount greater than 20% (wt.%) of the composition, or from about 20% to about 50%, or 20% to about 45%, or from 20% to about 40%, or from 20% to about 35%, or from 20% to about 30%.[0100| 18. The carbohydrate composition of any preceding claim wherein the weight percentage of the 1,6 linkages are in amount from 20% to about 30% or from about 20% to about 29%, or to about 28%, or to about 27%, or to about 26%, or to about 25%.

[0101] 19. The carbohydrate composition of any preceding claim wherein the weight percentage of the 1,6 linkages are in an amount from about 21% to about 30%, or from about 22% to about 30%, or from about 23% to about 30%, or from about 23% to about 30% or to about 24% to about 30%.

[0102] 20. The carbohydrate composition of preceding claim wherein the weight percentage of the 1,6 linkages are in amount from about 22% to about 28% or from about 23% to about 27%, or from about 24% to about 26%.

[0103] 21. The carbohydrate composition of any preceding claim wherein the (1,6 +1,4) to 1,3 linkages are from 5 to about 30 or from 5 to about 25 or from 5 to about 20 from 5 to about 15.

[0104] 22. The carbohydrate composition of any preceding claim wherein the ratio of the (1,6 +1,4) to 1,3 linkages is from 5 to about 10, or from about 6 to about 10.

[0105] 23. The carbohydrate composition of preceding claim wherein the (1 ,6 +1 ,4) to 1,3 linkages is from 5 to about 10 or from 5 to about 9 or from 5 to about 8.

[0106] 24. The carbohydrate composition of any preceding claim wherein the (1,6 +1,4) to 1,3 linkages is about 6 to about 9 or from about 6 to about 8.

[0107] 25. The carbohydrate composition of any preceding claim wherein a ratio of1,6 to 1,3 linkages greater than about 3 or greater than about 4, or greater than about 5.[0108| 26. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from about 3 to about 8 or from about 4 to about a, or from 5 to about 8

[0109] 27. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from about 3 to about 7 or from about 3 to about 6.

[0110] 28. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from to about 4 to about 7 or from about 4 to about 6.

[0111] 29. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from to about 4.5 to about 7 or from about 4.5 to about 6.

[0112] 30. The carbohydrate composition of any preceding claim wherein a ratio of1,6 to 1,4 linkages from greater than about 3

[0113] 31. The carbohydrate composition of any preceding claim wherein a ratio of1,6 to 1,4 linkages or greater than about 4.

[0114] 32. The carbohydrate composition of any preceding claim wherein a ratio of1,4 to 1 / 2 linkages less than about 1 or less than 0.95 or less than 0.9, or from 0.10 to 0.95, or from 0.20 to 0.95, or from 0.30 to 0.95, or from 0.40 to 0.95, or from 0.50 to 0.95 or from 0.60 to 0.95 or from 0.70 to 0.95.

[0115] 33. The carbohydrate composition of any preceding claim wherein a sum of1,6 + 1,4 linkages greater than about 28%, or greater than about 29%, or greater than about 30%.

[0116] 34. The carbohydrate composition of any preceding claim wherein the percentage of 1,6 linkages is greater than the percentage 1,2 linkages.

[0117] 35. The carbohydrate composition of any preceding claim wherein the percentage of 1,6 linkages is greater than the percentage of 1,4 linages.

[0118] 36. The carbohydrate composition of any preceding claim wherein the percentage of 1,6 linkages is greater than the percentage of 1,2 linkages, and the percentage of 1,6 linkages is greater than the percentage of 1,4 linkages, and the percentage of 1,2 linkages is greater than the percentage of 1,4 linkages.

[0119] 37. The carbohydrate composition of any preceding claim wherein a weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 (“DP3 to DP5”) is greater than about 25%, or greater than about 30%, or greater than about 35%, or greater than about 40%.

[0120] 38. The carbohydrate composition of claim 38 wherein the DP3 to DP5 is from about 25% to about 40%, or from about 25% to about 35%.

[0121] 39. The carbohydrate composition of claim 38 wherein the DP3 to DP5 is from about 26% to about 35%, or from about 27% to about 35%, or from about 28% to about 35%.

[0122] 40. The carbohydrate composition of claim 38 wherein the DP3 to DP5 is from about 28% to about 34%, or from about 28% to about 33%, or from about 28% to about 32%.

[0123] 41. The carbohydrate composition of any preceding claim wherein a weight percentage of glucose polymers having a degree of polymerization greater than 6 (“DP6+”) is less than 50%, or less than 45%, or from about 40% to about 50%, from about 40% to about 45%.

[0124] 42. The carbohydrate composition of any preceding claims wherein a ratio of the weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 to weight percentage of glucose polymers having a degree of polymerization greater than 6 (“DP3 to DP5 / DP6+”) is greater than about 0.5, or from about 0.5 to about 2.0, or from about 0.5 to about 1.5, or from about 0.5 to about 1.0.

[0125] 43. The carbohydrate composition of any preceding claim further comprising a total dietary fiber content greater than about 30% (wt.%), or greater than about 40%, or greater than about 50%, or greater than about 60%, or greater than about 70%, or from about 30% to about 80%, or to about 70% or to about 60%, or to about 50%, or to about 40%, or 40% to about 80%, or to about 70% or to about 60%, or to about 50%, or 50% to about 80%, or to about 70% or to about 60%, or 60% to about 80%, or to about 70%.

[0126] 44. An intermediate carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages wherein the weight percentage content of the glucose polymers having a degree of polymerization greater than 6 (“DP6+”) is less than about 25% or less than 20% or less than about 15%, or from about 1% or from about 3% or from about 5% to about 25%, or from aboutl%, or from about 3%, or from about 5% to about 20%, or from about 1% or from about 3% or from about 5% to about 15%.

[0127] 45. The intermediate carbohydrate composition of claim 44 wherein the DP6+ content is from about 6% to about 15% or from about 7% to about 15%, or from about 8% to about 15%, or from about 9% to about 15%, or from about 10% to about 15%.

[0128] 46. The intermediate carbohydrate composition of claim 45 wherein theDP6+ content is from about 5% to about 14%, or from about 5% to about 13% or from about 5% to about 12% or from about 5% to about 11%.

[0129] 47. The intermediate carbohydrate composition of any one of claims 44 to46 wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to 1,3 linkages is greater than 3, or greater than 4, or greater than 5.

[0130] 48. The intermediate carbohydrate composition of claim 44 to 46 wherein the (1,6 +1,4) to 1,3 ration is from 4 to 6, or from 5 to 6.[01311 49. The intermediate carbohydrate composition of any one of claims 44 to 48 wherein a weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 (“DP3 to DP5”) is greater than about 25%, or greater than about 30%, or greater than about 35%, or greater than about 40%.

[0132] 50. The intermediate carbohydrate composition of claim 44 to 49 wherein the DP3 to DP5 is from about 25% to about 40%, or from about 25% to about 35%.

[0133] 51. The intermediate carbohydrate composition of claim 44 to 50 wherein the DP3 to DP5 is from about 26% to about 35%, or from about 27% to about 35%, or from about 28% to about 35%.

[0134] 52. The intermediate carbohydrate composition of claim 44 to 51 the DP3 to DP5 is from about 28% to about 34%, or from about 28% to about 33%, or from about 28% to about 32%.

[0135] 53. The intermediate carbohydrate composition of any one of claims 44 to52 wherein a ratio of glucose polymers having a degree of polymerization in the range from DP3 to DP5 to the glucose polymers having a degree of polymerization DP6+ (“(DP3 to DP5) / DP3”) is greater than about 2.0 or greater than 3.0, or from about 2.0 to 5.0 or from about 2.0 to 4.0.

[0136] 54. A method of making a carbohydrate composition comprising:

[0137] a) mixing a solution comprising glucose syrup having a dry solids content of at least about 50%, or at least about 60% or at least about 70%, or at least about 80% dry solids or from about 60% to about 90% or from about 70% to about 90% or from about 70% to about 80% with acid wherein the acid is in an amount from about 0.01% to 0.1 % by weight of the solution

[0138] b) heating the solution to evaporate a portion of the liquid in the glucose syrup to increase solids content of the syrup in an amount by percentage of at least about 10% or at least about 20% or least about 30% or at least about 40% at a pressure from about 0.75 bar to about 1.50 bar, or about 0.8 bar to about 1.2 bar, or from about 0.9 to about 1.1 bar to obtain an intermediate carbohydrate; optionally wherein the intermediate composition is as described in any foregoing claim;

[0139] c) decreasing the pressure on the mixture to less than 0.25 bar, or less than 0.1 bar, or less than 0.05 bar for a time less than 10 minutes, or less than 5 minutes, or less than 1 minute to obtain the carbohydrate composition optionally wherein the carbohydrate composition is as described in any foregoing claim.

[0140] 55. The method of claim 54 wherein the glucose syrup has from about 65% to about 75% dry solids.

[0141] 56. The method of claim 54 or 55 wherein the glucose syrup has DE greater than about 60DE or greater than about 80DE or greater than about 90DE, wherein, preferably, the DE is at greater than about 80DE, or greater than about 90DE.

[0142] 57. The method of any one of claims 54 to 56 claim wherein the acid is selected from the group consisting of hydrochloric acid, sulfuric acid.

[0143] 58. The method of any one of claims 54 to 57 wherein the acid is in an amount from about 0.01% to about 0.09%, or from about 0.01% to about 0.08%, or from about 0.01% to about 0.07%, of the solution, or from about 0.02% to about 0.1% or from about 0.03% to about 0.1% or from about 0.02% to about 0.08%, or from about 0.03% to about 0.07%.

[0144] 59. The method of any one of claims 54 to 58 claim wherein the pH of the mixture is less than 2, or is less than 1, or from 0.1 to 2.

[0145] 60. The method of one of claims 54 to 59 wherein during the heating the solution step b) is for a time from about greater than 1 hour or from 1.1 hours to about 4 hours or from about 1.1 hours to about 3 hour, or from about 1.5 hour to a 2.5 hour.

[0146] 61. The method of any one of claims 54 to 60 wherein the intermediate carbohydrate composition has a dry solids content of from 80% to 99%%.

[0147] 62. The method of any one of claims 54 to 61 wherein the intermediate carbohydrate composition has a dry solids content from 81% to 95% or from 82% to 95%, or from 83% to 95% or from 84% to 95%, or from 85% to 95%.

[0148] 63. The method of any one of claims 54 to 62 wherein the intermediate carbohydrate has a dextrose equivalent from about 5 ODE to about 70DE, or from about 55DE to about 65DE.

[0149] 64. The method of any one of claims 54 to 63 wherein the during the decreasing pressure step the intermediate carbohydrate composition is heated to a temperature from about 100° C to 190° C, or from about 110° or from 120° to 190° C or from or from about 120°, or from 125° to 185° C.

[0150] 65. The method of any one of claims 54 to 64 wherein the intermediate carbohydrate is a carbohydrate composition as described in claims 44 to 53.

[0151] 66. The method of any preceding claim wherein the carbohydrate composition is as a carbohydrate composition as described in any one of claims 1 to 44.

[0152] 67. A composition made by a process as described in any one of claims 54 to 64.

[0153] 68. The composition of claim 67 and as described in any one of claims 1 to44.

[0154] 69. An edible composition comprising the carbohydrate composition of any one of claims 1 to 44.

[0155] 70. The edible composition of claim 69 being selected from the group consisting of cereals, edible bars, granola bars, snack bars, cold pressed bars, confectioneries, beverages, and savory products, fruit preparations used for fillings, pastries, pastries fillings, hygienic compositions, pharmaceutical compositions, pro-biotic compositions, and pro-biotic compositions.

[0156] 71. The edible composition of claim 69 or 70 further comprising a second edible ingredient and wherein the carbohydrate composition is in an amount (by weight percent of the edible composition) from 1% to 50%, or to 45%, or to 40%, or to 35%, or to 30%, or to 25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2%.

[0157] 72. The edible composition of claim 70 or 71 wherein the edible ingredient is selected from the group consisting of starches (including high amylose and low amylose variants), proteins (from animal and plant sources), sweeteners (including nutritive, nonnutritive, and high potency sweeteners), gums, hydrocolloids, water, flavorings, seasoning, preservatives, leavening agents, coloring agents, flavors, fragrances, and essences.

[0158] 73. The edible composition of any one of claims 70 to 72 wherein the edible composition is a food composition selected from the group consisting of bread, pastries, cookies, muffins, pizza doughs, baked goods, meats, alternative meat product; dry soup mixes, bakery mixes, frosting mixes, spice mixes and blends, coverage powders, condiments, gravy mixes, sauce mixes and frozen dairy foods, and fat mimetics.

[0159] 74. Use of a carbohydrate composition as described in any one of claim 1 to 44 in edible composition in a manner selected from the group consisting reducing the calorie content of an edible composition, as a tableting compound, as an anti-caking agents, as a protective coating, as an agglomeration aid wherein the carbohydrate composition is in an amount (by weight percent of the edible composition) from 1% to 50%, or to 45%, or to 40%,or to 35%, or to 30%, or to 25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2%.

[0160] 75. Use of a carbohydrate composition as described in claim 74 wherein the use is to reduce the calorie content of an edible composition, and wherein the carbohydrate composition replaces a nutritive sweetener in the edible composition in an amount up to 100%, up to 90%, up to 80%, up to 75%, up to 70%, up to 60%, up to 50%, up to 40%, up to 30%, up to 25%, up to 20%, up to 15%, up to 10%, or up to 5% or from 1% to 100% or from 1% to 75% or from 1% to 67%, or from 1% to 60%, or from 1% to 50%, or from 1% to 40%, or from 1% to 33, or from 1% to 30%, or from 1% to 25%, or from 1% to 20%, or from 1% to 15%, or from 1% to 10%, or from 1% to 5%.

[0161] 76. A method making a food composition comprising mixing a carbohydrate composition as described in any one of claims 1 to 44 in an amount from 1% to 50%, or to 45%, or to 40%, or to 35%, or to 30%, or to 25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2% and a second edible ingredient.

[0162] 77. The method of claim 76 wherein the second edible ingredient is selected from the group consisting of starches (including high amylose and low amylose variants), proteins (from animal and plant sources), sweeteners (including nutritive, non-nutritive, and high potency sweeteners), gums, hydrocolloids, water, flavorings, seasoning, preservatives, leavening agents, coloring agents, flavors, fragrances, and essences.

[0163] The technology disclosed in this specification can be better understood with reference to the following examples, which are not intended to limit the full scope of the disclosed technology.EXAMPLE 1 - PREPARATION OF INTERMEDIATE CARBOHYDRATE (STEP 1 REACTION)

[0164] Embodiments of an intermediate carbohydrate composition as described in this specification were made as follows. Liquid dextrose (71% wt.%, dry solids basis) was mixed with from 0.1% to 0.2% (wt.%) IM hydrochloric acid to form a solution (acid concentration of solution was between 0.03% to 0.07% wt.%). The solution was heated (preheated heating plate) in an open reaction at ambient air pressure (about 1 atm) to a temperature sufficient for the water to evaporate (but not more than 150° C). Heating continued until the dry solidscontent of the solution increased to between about 86% and about 88% (wt.% dry solids basis). The water loss was monitored by tracking the system’s weight change. The reaction was stopped by adding deionized water equal to the water lost during heating forming an intermediated carbohydrate composition. Part of the intermediate carbohydrate composition was reserved for preparing the carbohydrate composition.EXAMPLE 2 - PREPARATION OF CARBOHYDRATE COMPOSITION (STEP 2 REACTION)

[0165] Intermediate carbohydrate composition was prepared as described above and was transferred to a Rotovap flask. The flask was put into the Rotovap set to a pressure of 95mBar, and a temperature of 130° C for up to 5~10min. The TDF% in final product can be vary (70%, 60%, etc.) by adjusting time, temperature, etc. All evaporation processes produced a dry material was collected and evaluated for total dietary fiber and saccharide length distribution.EXAMPLE 3 - METHODS FOR MEASURED SACCHARIDE DISTRIBUTION AND TOTAL DIETARY FIBER

[0166] Intermediate carbohydrate composition of Example 1 and carbohydrate compositions of Example 2 were evaluated to determine (1) glycosidic linkage profile, (2) total dietary fiber content, and (3) the distribution of the degree of polymerization of the carbohydrates. Also, the glycosidic linkage profile and distribution of the degree of polymerization of the various on sale carbohydrate compositions were measured to compare with the intermediate carbohydrate compositions of Example 1 and the carbohydrate compositions of Example 2.

[0167] Within this specification glycosidic linkage analysis was done using partially methylated alditol acetates (PMAA) derivatization method for GC-MS. Samples (3 mg) were dissolved in 500 pl DMSO, 200 pl n-butyl lithium were added, and tubes were incubated for 40 minutes. Methyl iodide (300 pl) was added and stirred for 1 hour. The resulting mixtures were partitioned with deionized water and chloroform. The chloroform layer was separated and dried under a stream of nitrogen. Samples were hydrolyzed with 2M TFA for 1 hour at 121° C containing 1 mg / ml inositol as an internal standard. The samples were then dried under the stream of nitrogen. Dry samples were reduced with 100 pl of IM ammonium hydroxide with 20 mg / ml of sodium borodeuteride in DMSO for 90 minute at 40° C. The reaction was quenched with glacial acetic acid. Samples were O-acetylated with 100 pl of 1- methylimidazole and 500 pl of acetic anhydride. The resulting partially methylated alditolacetates were partitioned with deionized water and methylene chloride. The methylene chloride layer was separated and dried under a stream of nitrogen. Samples were dissolved in 1 ml acetone and analyzed by GC-MS (GC - Agilent 7890A equipped with FID detector, MS - Agilent 5975C, column SP-2330).10168] Within this specification carbohydrate (DP) distribution analysis was done as follows. Samples were prepared at 1% solids in HPLC grade water and analyzed on an Agilent 1260 HPLC-RID instrument. HPLC grade water was the mobile phase with a flow rate of 0.5 ml / minute using a Bio-Rad Aminex HPX-42A column for separation. Samples were reported in area percent.[0169| Within this specification, total dietary fiber analysis was done as follows. Samples were prepared by adding one 1g of sample per 40 ml of pancreatic alpha-amylase / AMG mixture to a 250mL Fisherbrand soda glass, wide mouth bottle. Bottles were shaken in a Grant OLS 200 shaking incubation bath at 37° C and 150 rpm in orbital motion for 16 hours. After 16 hours, removed all bottles and added 3.0 mL of 0.75 M Tris buffer solution to terminate the reaction. Slightly loosened the cap and placed in the water bath at temperature in the range from 95° to 100° C for 20 minutes. To bottle solution added 0.1 mL of protease solution and incubate at 60° C for 30 minutes. Adjusted pH to approximately 4.3 by adding 4.0 mL of 2 M acetic acid. With 1.0 mL of D-sorbitol as internal standard. The total dietary fiber was analyzed by HPLC (Waters Sugar-Pak column with flow rate 0.5 mL / min) after deionization using mix of Amberlite FPA 53 (OH-) and Ambersep 200 (H+).EXAMPLE 4 - MEASUREMENTS OF TOTAL SACCHARIDE DISTRIBUTION AND TOTAL DIETARY FIBER OF EMBODIMENTS AND COMPARATIVE PRODUCTS

[0170] Carbohydrate composition Sample 2 (of Example 2) had total dietary fiber content of 70%. Carbohydrate composition of Sample 1 (of Example 2) had total dietary fiber of 60%. Results of the evaluation carbohydrate linkage profile and the distribution of the degree of polymerization of the carbohydrate are reported below.

[0171] Table 1 reports the distribution of the intermediate carbohydrate composition from Example 1 and Carbohydrate Composition Sample 1 and Sample 2, from Example 2.Table 1Comparison of Distribution of Degree of Polymerization

[0172] As shown in Table 1 the reaction of Example 1 produces a carbohydrate composition having relatively low number carbohydrates with a high degree of polymerization - i.e. degree of polymerization greater 6 (“DP6”). The reaction 2 of Example 2 is a polymerization reaction that obtains TDF levels greater than 70% (Sample 2).

[0173] Table 2 reports the glycosidic linkage profile of the intermediate carbohydrate composition of Example 1 and the Sample 1 and Sample 2 of the carbohydrate composition of Example 2.Table 2 glycosidic Linkage Profile of the Material of Examples 1 and 2

[0174] Table 2 reports the digestion resistant or slowly digestible oligosaccharides content by reference to relatively low amount of 1,4 linkages and elevated amount of 1,6 linkages.10175] Table 3 compares the glycosidic linkages of carbohydrate composition Sample 2 from Example 2 with prior art carbohydrate compositions. Product 2B of US Patent Publication 20160015065, Promitor® soluble fiber (available from Tate & Lyle) and Fibersol® soluble fiber (available from ADM), were chosen as comparators because they are carbohydrate compositions having roughly 70% total dietary fiber.Table 3Glycosidic Linkage Comparison Between Sample 2 And Others

[0176] Table 3 illustrates that carbohydrate composition Sample 2 (from Example 2) has relatively higher 1,6 linkages and relatively lower 1, 3, and 1,4 linkages in an 70% total dietary fiber composition.

[0177] Table 4 compares the degree of polymerization of Sample 2 of the intermediate carbohydrate composition (from Example 1) with 2B of US Patent Publication 20160015065, Promitor® soluble fiber (available from Tate & Lyle) and Fibersol® soluble fiber. The comparative samples are other available carbohydrate compositions having 70% total dietary fiber.Table 4.Distribution of the Degree of Polymerization Comparing Carbohydrate Compositions with Intermediate Carbohydrate Composition and 63DE Glucose Syrup

[0178] Table 5 shows that the intermediate carbohydrate composition is also a unique carbohydrate composition relative to other soluble fiber compositions with high percentage of oligosaccharides having degree of polymerization from 3 to 5.

[0179] Table 5 compares the degree of polymerization of Sample 2 of the carbohydrate composition (from Example 2) with 2B of US Patent Publication 20160015065, polydextrose, Promitor® soluble fiber (available from Tate & Lyle) and Fibersol® soluble fiber. The comparative samples are other available carbohydrate compositions having 70% total dietary fiber.

[0180] With reference to Figure 1, it is seen for each degree of polymerization (DE 42 syrup is the bar on the left, DE 62 syrup is the bar in the middle, and the 2-stage preliminary intermediate is the bar on the on the right) that an embodiment of an intermediate carbohydrate composition has similar distribution of oligosaccharides, by reference to degree of polymerization, as a commercially available DE63 Glucose Syrup. Not specifically, the left bar (2-stage preliminary intermediate composition) is an embodiment of the intermediate carbohydrate composition. But, in addition to the differences of degree of polymerization seen, glucose syrups, being made from the controlled enzymatic hydrolysis of starch are substantially comprised of 1-4 linkages and do not have the various glucose linkages of the intermediate carbohydrate.Table 5.Distribution of the Degree of Polymerization of Various Carbohydrate Compositions[01811 Table 5 shows that carbohydrate composition Sample 2 has uniquely high percentage of oligosaccharides having degree of polymerization from 3 to 5 compared to Promitor® soluble fiber, Fibersol® DLQ soluble fiber and embodiments from US Pat. Pub. 2016- 0015065. Showing that the predominant component of composition is a digestion resistant or slowly digestible oligosaccharide having intermediate change length and comparatively reduced amount of high degree of polymerization (DP6+) oligosaccharides. Notably the predominance of oligosaccharides having DP 3 to 5 exists even though the reaction of Example 2 is a polymerization that increases the oligosaccharides having DP6+.EXAMPLE 5 - REACTION VARIATIONS

[0182] Example 5 varies the reaction conditions to make the intermediate and final carbohydrate compositions as said in Examples 1 and 2. The variations are said in below, called Samples A to E. Any conditions said in Examples 1 and 2 that are not explicitly said to be changed below are the same as said in Examples 1 and 2. For each sample, reduced pressure conditions can be achieved using Rotovap, glass reactor with vacuum pump or similar.

[0183] Sample A: The step 1 reaction was run at 120° C for 4 hours at 900 mBar. Step 2 reaction was run 150° C for 5 to 10 minutes at sample pressure as said in Example 2.

[0184] Sample B: The step 1 reaction was run at 130° C for 3 hours at 900 mBar. The step 2 reaction was done at the same pressure as said in Example 2 but was run at 180° for 1 to 2 minutes.

[0185] Sample C: The step 1 reaction was run at 130° C for 1.5 hours at 900 mBar. The step 2 reaction was done at the same pressure as said in Example 2 but was run at 180° C for 1 to 2 minutes.

[0186] Sample D: The step 1 reaction was run at 130° C for 1.5 hours at 900 mBar. The step 2 reaction was done at the same pressure as said in Example 2 but was run at 200° C for 2 to 5 minutes.

[0187] Sample E: The step 1 reaction was run at 130° C for 3 hours at 900 mBar. The step 2 reaction was done at the same pressure as said in Example 2 but was run at 200° C for 2 to 5 minutes.

[0188] Structure of the carbohydrate composition (composition following the step 2 reaction) are said in Table 6. Total dietary fiber and linkage types were evaluated using methods described in this specification.Table 6

Claims

CLAIMSWhat is claimed is:

1. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to the 1,3 linkages is at least 4.9 or at least 5, or greater than 5 or from 4.9, or from 5.0, or from 5.1 to 10, or from or from 4.9, or from 5.0, or from 5.1 to 9, or from 4.9, or from 5.0, or to 8, or from 4.9, or from 5.0, or to 7.5; wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues; wherein, optionally, the composition consists essentially of the glucose polymers or consist of the glucose polymers.

2. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and wherein a ratio of 1,6 to 1,3 linkages is greater than about 3 or greater than about 4, or greater than about 5 wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues; wherein optionally the composition consists essentially of the glucose polymers or consist of the glucose polymers.

3. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and wherein a ratio of 1,6 to 1,4 linkages is greater than 4.1, or from 4.1 to 10, or from 4.1 to 9, or from 4.1 to 8, or from 4.1 to 7, from 4.1 to about 6 or from 4.1 to about 5wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues; wherein optionally the composition consists essentially of the glucose polymers or consist of the glucose polymers.

4. A carbohydrate composition comprising a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and wherein a ratio of 1,4 to 1,2 is less than about 1, or less than 1, or less than 0.95 wherein, optionally, the polymers are comprised of greater than 90% glucose residues greater than 95% glucose residues, or greater than 97%, greater than 98%, or greater than 99% glucose residues; wherein optionally the composition consists essentially of the glucose polymers or consist of the glucose polymers.

5. The carbohydrate composition of claims 1 and 2.

6. The carbohydrate composition of claims 1 and 3.

7. The carbohydrate composition of claims 1 and 4.

8. The carbohydrate composition of claims 2 and 3.

9. The carbohydrate composition of claims 2 and 4.

10. The carbohydrate composition of claims 3 and 4.

11. The carbohydrate composition of claims 1, 2, and 3.

12. The carbohydrate composition of claims 1, 2, and 4.

13. The carbohydrate composition of claims 1, 3, and 4.

14. The carbohydrate composition of claims 2, 3, and 4.

15. The carbohydrate composition of claims 1 , 2, 3, and 4.

16. A carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of 1-2, 1-3, 1-4, and 1-6 linkages and having one or more properties selected from the group consisting ofa) a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to the 1,3 linkages is greater than 5 b) a ratio of 1,6 to 1,3 linkages is greater than about 3 or greater than about 4, or greater than about 5 c) a ratio of 1,6 to 1,4 linkages is greater than 4.1, or from 4.1 to 10, or from 4.1 to 9, or from 4.1 to 8, or from 4.1 to 7, from 4.1 to about 6 or from 4.1 to about 5 and d) a ratio of 1,4 to 1,2 is less than about 1, or less than 1, or less than 0.95, wherein, optionally, the composition consists essentially of the glucose polymers or consist of the glucose polymers.

17. The carbohydrate composition of any preceding claim wherein the weight percentage of the 1,6 linkages in the composition are in an amount greater than 20% (wt.%) of the composition, or from about 20% to about 50%, or 20% to about 45%, or from 20% to about 40%, or from 20% to about 35%, or from 20% to about 30%.

18. The carbohydrate composition of any preceding claim wherein the weight percentage of the 1,6 linkages are in amount from 20% to about 30% or from about 20% to about 29%, or to about 28%, or to about 27%, or to about 26%, or to about 25%.

19. The carbohydrate composition of any preceding claim wherein the weight percentage of the 1,6 linkages are in an amount from about 21% to about 30%, or from about 22% to about 30%, or from about 23% to about 30%, or from about 23% to about 30% or to about 24% to about 30%.

20. The carbohydrate composition of preceding claim wherein the weight percentage of the 1,6 linkages are in amount from about 22% to about 28% or from about 23% to about 27%, or from about 24% to about 26%.

21. The carbohydrate composition of any preceding claim wherein the (1,6 +1,4) to 1,3 linkages are from 5 to about 30 or from 5 to about 25 or from 5 to about 20 from 5 to about 15.

22. The carbohydrate composition of any preceding claim wherein the ratio of the (1,6 +1,4) to 1,3 linkages is from 5 to about 10, or from about 6 to about 10.

23. The carbohydrate composition of preceding claim wherein the (1,6 +1,4) to 1,3 linkages is from 5 to about 10 or from 5 to about 9 or from 5 to about 8.

24. The carbohydrate composition of any preceding claim wherein the (1,6 +1,4) to 1,3 linkages is about 6 to about 9 or from about 6 to about 8.

25. The carbohydrate composition of any preceding claim wherein a ratio of 1,6 to 1,3 linkages greater than about 3 or greater than about 4, or greater than about 5.

26. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from about 3 to about 8 or from about 4 to about a, or from 5 to about 827. The carbohydrate composition of any preceding claim wherein the ratio of 1 ,6 to 1 ,3 linkages is from about 3 to about 7 or from about 3 to about 6.

28. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from to about 4 to about 7 or from about 4 to about 6.

29. The carbohydrate composition of any preceding claim wherein the ratio of 1,6 to 1,3 linkages is from to about 4.5 to about 7 or from about 4.5 to about 6.

30. The carbohydrate composition of any preceding claim wherein a ratio of 1,6 to 1,4 linkages from greater than about 331. The carbohydrate composition of any preceding claim wherein a ratio of 1 ,6 to 1 ,4 linkages or greater than about 4.

32. The carbohydrate composition of any preceding claim wherein a ratio of 1,4 to 1 / 2 linkages less than about 1 or less than 0.95 or less than 0.9, or from 0.10 to 0.95, or from 0.20 to 0.95, or from 0.30 to 0.95, or from 0.40 to 0.95, or from 0.50 to 0.95 or from 0.60 to 0.95 or from 0.70 to 0.95.

33. The carbohydrate composition of any preceding claim wherein a sum of 1,6 + 1,4 linkages greater than about 28%, or greater than about 29%, or greater than about 30%.

34. The carbohydrate composition of any preceding claim wherein the percentage of 1,6 linkages is greater than the percentage 1,2 linkages.

35. The carbohydrate composition of any preceding claim wherein the percentage of 1,6 linkages is greater than the percentage of 1,4 linages.

36. The carbohydrate composition of any preceding claim wherein the percentage of 1,6 linkages is greater than the percentage of 1,2 linkages, and the percentage of 1,6 linkages isgreater than the percentage of 1,4 linkages, and the percentage of 1,2 linkages is greater than the percentage of 1,4 linkages.

37. The carbohydrate composition of any preceding claim wherein a weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 (“DP3 to DP5”) is greater than about 25%, or greater than about 30%, or greater than about 35%, or greater than about 40%.

38. The carbohydrate composition of claim 38 wherein the DP3 to DP5 is from about 25% to about 40%, or from about 25% to about 35%.

39. The carbohydrate composition of claim 38 wherein the DP3 to DP5 is from about 26% to about 35%, or from about 27% to about 35%, or from about 28% to about 35%.

40. The carbohydrate composition of claim 38 wherein the DP3 to DP5 is from about 28% to about 34%, or from about 28% to about 33%, or from about 28% to about 32%.

41. The carbohydrate composition of any preceding claim wherein a weight percentage of glucose polymers having a degree of polymerization greater than 6 (“DP6+”) is less than 50%, or less than 45%, or from about 40% to about 50%, from about 40% to about 45%.

42. The carbohydrate composition of any preceding claims wherein a ratio of the weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 to weight percentage of glucose polymers having a degree of polymerization greater than 6 (“DP3 to DP5 / DP6+”) is greater than about 0.5, or from about 0.5 to about 2.0, or from about 0.5 to about 1.5, or from about 0.5 to about 1.0.

43. The carbohydrate composition of any preceding claim further comprising a total dietary fiber content greater than about 30% (wt.%), or greater than about 40%, or greater than about 50%, or greater than about 60%, or greater than about 70%, or from about 30% to about 80%, or to about 70% or to about 60%, or to about 50%, or to about 40%, or 40% to about 80%, or to about 70% or to about 60%, or to about 50%, or 50% to about 80%, or to about 70% or to about 60%, or 60% to about 80%, or to about 70%.

44. An intermediate carbohydrate composition comprising: a plurality of glucose polymers comprising a mixture of l-2, 1-3, 1-4, and 1-6 linkages wherein the weight percentage content of the glucose polymers having a degree of polymerization greater than 6 (“DP6+”) is less than about 25% or less than 20% or less than about 15%, or from about 1% or from about3% or from about 5% to about 25%, or from about 1%, or from about 3%, or from about 5% to about 20%, or from about 1% or from about 3% or from about 5% to about 15%.

45. The intermediate carbohydrate composition of claim 44 wherein the DP6+ content is from about 6% to about 15% or from about 7% to about 15%, or from about 8% to about 15%, or from about 9% to about 15%, or from about 10% to about 15%.

46. The intermediate carbohydrate composition of claim 45 wherein the DP6+ content is from about 5% to about 14%, or from about 5% to about 13% or from about 5% to about 12% or from about 5% to about 11%.

47. The intermediate carbohydrate composition of any one of claims 44 to 46 wherein a ratio of a sum of the 1,6 and the 1,4 linages (“(1,6 +1,4)”) to 1,3 linkages is greater than 3, or greater than 4, or greater than 5.

48. The intermediate carbohydrate composition of claim 44 to 46 wherein the (1,6 +1,4) to 1,3 ration is from 4 to 6, or from 5 to 6.

49. The intermediate carbohydrate composition of any one of claims 44 to 48 wherein a weight percentage sum of glucose polymers having a degree of polymerization from 3 to 5 (“DP3 to DP5”) is greater than about 25%, or greater than about 30%, or greater than about 35%, or greater than about 40%.

50. The intermediate carbohydrate composition of claim 44 to 49 wherein the DP3 to DP5 is from about 25% to about 40%, or from about 25% to about 35%.

51. The intermediate carbohydrate composition of claim 44 to 50 wherein the DP3 to DP5 is from about 26% to about 35%, or from about 27% to about 35%, or from about 28% to about 35%.

52. The intermediate carbohydrate composition of claim 44 to 51 the DP3 to DP5 is from about 28% to about 34%, or from about 28% to about 33%, or from about 28% to about 32%.

53. The intermediate carbohydrate composition of any one of claims 44 to 52 wherein a ratio of glucose polymers having a degree of polymerization in the range from DP3 to DP5 to the glucose polymers having a degree of polymerization DP6+ (“(DP3 to DP5) / DP3”) is greater than about 2.0 or greater than 3.0, or from about 2.0 to 5.0 or from about 2.0 to 4.0.

54. A method of making a carbohydrate composition comprising:a) mixing a solution comprising glucose syrup having a dry solids content of at least about 50%, or at least about 60% or at least about 70%, at least about 80% dry solids or from about 60% to about 90% or from about 70% to about 90% or from about 70% to about 80% with acid wherein the acid is in an amount from about 0.01% to 0.1 % by weight of the solution b) heating the solution to evaporate a portion of the liquid in the glucose syrup to increase solids content of the syrup in an amount by percentage of at least about 10% or at least about 20% or least about 30% or at least about 40% at a pressure from about 0.75 bar to about 1.50 bar, or about 0.8 bar to about 1 .2 bar, or from about 0.9 to about 1.1 bar to obtain an intermediate carbohydrate; optionally wherein the intermediate composition is as described in any foregoing claim; c) decreasing the pressure on the mixture to less than 0.25 bar, or less than 0.1 bar, or less than 0.05 bar for a time less than 10 minutes, or less than 5 minutes, or less than 1 minute to obtain the carbohydrate composition optionally wherein the carbohydrate composition is as described in any foregoing claim.

55. The method of claim 54 wherein the glucose syrup has from about 65% to about 75% dry solids.

56. The method of claim 54 or 55 wherein the glucose syrup has DE greater than about 60DE or greater than about 80DE or greater than about 90DE, wherein, preferably, the DE is at greater than about 80DE, or greater than about 90DE.

57. The method of any one of claims 54 to 56 claim wherein the acid is selected from the group consisting of hydrochloric acid, sulfuric acid.

58. The method of any one of claims 54 to 57 wherein the acid is in an amount from about 0.01% to about 0.09%, or from about 0.01% to about 0.08%, or from about 0.01% to about 0.07%, of the solution, or from about 0.02% to about 0.1% or from about 0.03% to about 0.1% or from about 0.02% to about 0.08%, or from about 0.03% to about 0.07%.

59. The method of any one of claims 54 to 58 claim wherein the pH of the mixture is less than 2, or is less than 1, or from 0.1 to 2.

60. The method of one of claims 54 to 59 wherein during the heating the solution step b) is for a time from about greater than 1 hour or from 1.1 hours to about 4 hours or from about 1.1 hours to about 3 hour, or from about 1.5 hour to a 2.5 hour.

61. The method of any one of claims 54 to 60 wherein the intermediate carbohydrate composition has a dry solids content of from 80% to 99%%.

62. The method of any one of claims 54 to 61 wherein the intermediate carbohydrate composition has a dry solids content from 81% to 95% or from 82% to 95%, or from 83% to 95% or from 84% to 95%, or from 85% to 95%.

63. The method of any one of claims 54 to 62 wherein the intermediate carbohydrate has a dextrose equivalent from about 50DE to about 70DE, or from about 55DE to about 65DE.

64. The method of any one of claims 54 to 63 wherein the during the decreasing pressure step the intermediate carbohydrate composition is heated to a temperature from about 100° C to 190° C, or from about 110° or from 120° to 190° C or from or from about 120°, or from 125° to 185° C.

65. The method of any one of claims 54 to 64 wherein the intermediate carbohydrate is a carbohydrate composition as described in claims 44 to 53.

66. The method of any preceding claim wherein the carbohydrate composition is as a carbohydrate composition as described in any one of claims 1 to 44.

67. A composition made by a process as described in any one of claims 54 to 64.

68. The composition of claim 67 and as described in any one of claims 1 to 44.

69. An edible composition comprising the carbohydrate composition of any one of claims 1 to 44.

70. The edible composition of claim 69 being selected from the group consisting of cereals, edible bars, granola bars, snack bars, cold pressed bars, confectioneries, beverages, and savory products, fruit preparations used for fillings, pastries, pastries fillings, hygienic compositions, pharmaceutical compositions, pro-biotic compositions, and pro-biotic compositions.

71. The edible composition of claim 69 or 70 further comprising a second edible ingredient and wherein the carbohydrate composition is in an amount (by weight percent of the edible composition) from 1% to 50%, or to 45%, or to 40%, or to 35%, or to 30%, or to 25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2%.

72. The edible composition of claim 70 or 71 wherein the edible ingredient is selected from the group consisting of starches (including high amylose and low amylose variants), proteins (from animal and plant sources), sweeteners (including nutritive, non-nutritive, and high potency sweeteners), gums, hydrocolloids, water, flavorings, seasoning, preservatives, leavening agents, coloring agents, flavors, fragrances, and essences.

73. The edible composition of any one of claims 70 to 72 wherein the edible composition is a food composition selected from the group consisting of bread, pastries, cookies, muffins, pizza doughs, baked goods, meats, alternative meat product; dry soup mixes, bakery mixes, frosting mixes, spice mixes and blends, coverage powders, condiments, gravy mixes, sauce mixes and frozen dairy foods, and fat mimetics.

74. Use of a carbohydrate composition as described in any one of claim 1 to 44 in edible composition in a manner selected from the group consisting reducing the calorie content of an edible composition, as a tableting compound, as an anti-caking agents, as a protective coating, as an agglomeration aid wherein the carbohydrate composition is in an amount (by weight percent of the edible composition) from 1% to 50%, or to 45%, or to 40%, or to 35%, or to 30%, or to 25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2%.

75. Use of a carbohydrate composition as described in claim 74 wherein the use is to reduce the calorie content of an edible composition, and wherein the carbohydrate composition replaces a nutritive sweetener in the edible composition in an amount up to 100%, up to 90%, up to 80%, up to 75%, up to 70%, up to 60%, up to 50%, up to 40%, up to 30%, up to 25%, up to 20%, up to 15%, up to 10%, or up to 5% or from 1% to 100% or from 1% to 75% or from 1% to 67%, or from 1% to 60%, or from 1% to 50%, or from 1% to 40%, or from 1% to 33, or from 1% to 30%, or from 1% to 25%, or from 1% to 20%, or from 1% to 15%, or from 1% to 10%, or from 1% to 5%.

76. A method making a food composition comprising mixing a carbohydrate composition as described in any one of claims 1 to 44 in an amount from 1% to 50%, or to 45%, or to 40%, or to 35%, or to 30%, or to 25%, or to 20%, or to 15%, or to 10%, or to 9%, or to 8%, or to 7%, or to 6%, or to 5%, or to 4%, or to 3%, or to 2% and a second edible ingredient.

77. The method of claim 76 wherein the second edible ingredient is selected from the group consisting of starches (including high amylose and low amylose variants), proteins(from animal and plant sources), sweeteners (including nutritive, non-nutritive, and high potency sweeteners), gums, hydrocolloids, water, flavorings, seasoning, preservatives, leavening agents, coloring agents, flavors, fragrances, and essences.

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