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Oxidation of carbohydrates by means of peroxidases and nitroxy radicals

A technology of carbohydrates and peroxidase, which is applied in the field of oxidation of carbohydrates with peroxidase and nitroxyl, which can solve the problems of unsuitable industrial scale application and uneconomical

Inactive Publication Date: 2007-01-10
CERESTAR HLDG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, existing methods are not economical nor suitable for industrial-scale applications

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Manufacture of gluconic acid and glucaric acid

[0048] 15 g of D-glucose (from Aldrich) were dissolved in 21.5 ml of demineralized water (=39.9% dry matter). 1.056 g TEMPO (from Aldrich) was added to the glucose solution. Add 0.0206g soybean peroxidase (SIGMA TM ), the reaction was carried out at 25° C. for 24 hours with stirring. Hydrogen peroxide (30%, Perhydrol from Merck TM ) was continuously added at a dose rate of 0.138 mmol / min. The pH was kept constant at 7 by adding 4M NaOH (from Merck).

[0049] After 24 hours, the reaction mixture was analyzed by HPLC. Samples were analyzed on two different columns at 75°C at 1ml / min: Shodex K-S-801 (Na + Form) column, carried out with water; Shodex KC-811 (H + form) column, with 0.01M H 2 SO 2 conduct. The two chromatograms obtained were used to determine the levels of glucuronic acid (4.4%), gluconic acid (86.5%), glucaric acid (6.8%) obtained by oxidation reactions.

Embodiment 2

[0050] Embodiment 2 Determination of aldehyde content in oxidized trehalose (test 1)

[0051] Oxidation process

[0052] For 20g D-trehalose (ASCEND from Cargill TM ) was carried out in laboratory experiments using soybean peroxidase / hydrogen peroxide and TEMPO (from Aldrich) as mediators. Use the following conditions:

[0053] -Dry matter D-trehalose: 40% d.s.

[0054] - Molar ratio TEMPO / primary alcohol functionality * : 1 / 40

[0055] -Soybean peroxidase (OrganicTec TM ): 10 000 units / mol primary OH

[0056] - Hydrogen peroxide (30% Perhydrol TM ): 0.01ml / min

[0057] - 4M sodium hydroxide solution for pH stat control at pH 7

[0058] - Reaction temperature: 25°C

[0059] * The primary alcohol function mentioned above has the formula -CH 2 -OH, but it can be abbreviated as "primary OH".

[0060] The reaction medium is continuously stirred with a magnetic stirrer. Samples were taken after increasing reaction times (10, 21, 28 and 36 hours) corresponding to the s...

Embodiment 3

[0070] Example 3 Determination of aldehyde content in oxidized trehalose (test 2)

[0071] Oxidation process

[0072] Selective C6-oxidation of 20 g of D-trehalose was carried out in laboratory experiments using soybean peroxidase / hydrogen peroxide and TEMPO (from Aldrich) as mediators.

[0073] Use the following conditions:

[0074] -Dry matter D-trehalose: 40% d.s.

[0075]-Molar ratio TEMPO / primary OH: 1 / 40

[0076] -Soybean peroxidase (OrganicTec TM ): 5000 units / mol primary OH

[0077] - Hydrogen peroxide (30% Perhydrol TM ): 0.01ml / min

[0078] - 4M sodium hydroxide solution for pH stat control at pH 5, pH 6, pH 7 and pH 8

[0079] - Reaction temperature: 25°C

[0080] Samples were removed after increasing the reaction time. The corresponding sodium hydroxide consumption is shown in Table 2.

[0081] Carboxyl and aldehyde determination

[0082] In addition to NaOH consumption, standard Blumenkrantz (specific uronic acid quantification) and HPLC methods were us...

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PUM

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Abstract

The invention provides a method of oxidising carbohydrates and / or carbohydrate derivatives having primary alcohol groups comprising contacting a reaction medium containing said carbohydrates and / or carbohydrate derivatives with a nitroxy radical mediator and a peroxidase enzyme, characterised in that the initial reaction medium contains at least 10% by weight carbohydrates and / or carbohydrate derivatives, in that the peroxidase enzyme is an oilseed peroxidase and in that a hydroperoxide and an alkali compound are gradually added to the reaction medium such that its pH is maintained at between 3.5 and 10.0 (pH-Stat); the invention also relates to the use of said method in a process for producing gluconic acid, glucaric acid and / or D-glucuronolactone.

Description

technical field [0001] The present invention relates to methods for the oxidation of carbohydrates and / or carbohydrate derivatives using peroxidases and nitroxyl mediators. In particular, the invention relates to methods for the selective oxidation of primary alcohol groups to carboxyl groups. Background of the invention [0002] Oxidation of primary alcohol groups on carbohydrates (and carbohydrate derivatives) leads to the formation of aldehydes (R'-CHO) and / or carboxyl groups (R'-COOH). [0003] The formation of aldehydes and carboxyl groups increases the reactivity, versatility and solubility of the resulting compounds, which therefore have a greater number of industrial applications (for example, in the food, textile and paper industries). As a result, there has been great interest in developing methods that allow selective oxidation of primary alcohol groups. One such approach involves the use of nitroxyradical mediators. [0004] Numerous nitroxy-mediated oxidation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/58C12P19/02C12P17/04C12P19/04
CPCC12P7/58C12P19/02C12P17/04
Inventor R·L·M·韦考特伦A·A·J·海伦
Owner CERESTAR HLDG
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