Amino acid derivatives and method for preparation thereof

Abstract

The present invention relates to a novel amino acid derivative represented by the chemical formula (3) and a method for preparing the same. (3) In the above chemical formula (3), R is selected from hydrogen, hydroxyl, C1 to C12 alkyl groups, C1 to C12 alkoxy groups, C2 to C12 alkenyl groups, C1 to C12 alkylamine groups, and C3 to C12 cycloalkyl groups.

Description

Technology Field

[0001] The present invention relates to a novel amino acid derivative and a method for preparing the same. Background Technology

[0002] Amino acids are the building blocks of proteins (peptides), and they are compounds that possess both a basic amino group (-NH2) and an acidic carboxyl group (-COOH). Most are colorless crystals and are highly soluble in water. Amino acids are representative amphoteric electrolytes and are important components of proteins. When proteins are hydrolyzed by acids or enzymes (pepsin, trypsin, erepsin), they become various types of amino acids; among these, those in which the amino group and the carboxyl group are bonded to the same carbon atom are called α-amino acids.

[0003] Most of the amino acids contained in animal bodies are α-amino acids. These amino acids combine in a specific sequence to form proteins. When amino acids combine, a water molecule is released to condense and form an -CO-NH- bond. This bond is called a peptide bond or an amide bond. The proteins we consume are hydrolyzed into smaller sizes by enzymes in the stomach and small intestine, breaking down into amino acids that are then absorbed into the body. These absorbed amino acids are rearranged in a specific sequence according to genetic information to be synthesized into the proteins that make up our bodies.

[0004] Essential amino acids cannot be synthesized in the body and must be obtained from food for survival. Since amino acids obtained from food are water-soluble, they do not require a special transport system. Essential amino acids are isoleucine, leucine, phenylalanine, lysine, methionine, threonine, tryptophan, and valine. Non-essential amino acids include alanine, asparagine, aspartic acid, glutamic acid, glutamine, glycine, proline, serine, and tyrosine. Arginine and histidine are essential during the growth period. All essential amino acids and most non-essential amino acids possess one or more asymmetric carbon atoms and exhibit photoactivity.

[0005] Amino acids have the function of forming proteins, participating in metabolism, and creating neurotransmitters. They are involved in the growth and maintenance of tissues. Furthermore, they serve as major components of hormones, enzymes, and antibodies. Each possesses its own unique function.

[0006] When RNA synthesizes proteins by linking specific amino acids according to the DNA code, the chemical structure of the amino acids controls the structure of the protein, and this form of the protein determines the protein's function.

[0007] Furthermore, amino acids are converted into energy through metabolism when necessary. In addition, glutamic acid, cysteine, and glycine form glutathione, an antioxidant. Histidine plays a role in hydrogen transfer at enzyme reaction sites and is an important amino acid for red blood cell production and maintaining healthy nerves. Tyrosine is used in the production of thyroid hormones. Methionine converts into S-adenosylmethionine and participates in DNA and neurotransmitter metabolism through methylation. Arginine is said to generate nitric oxide, which relaxes vascular muscles to lower blood pressure and inhibits platelet formation in arteries.

[0008] Amino acids such as tryptophan and tyrosine form neurotransmitters. Tryptophan produces serotonin, while tyrosine synthesizes norephedrine and adrenaline. In the brain, tryptophan induces drowsiness, while tyrosine provides more energy. In addition, glutamate and aspartic acid are excitatory neurotransmitters.

[0009] As such, amino acids perform important functions within the body, and a deficiency can affect the regulation of human metabolism. Therefore, research and development regarding the synthesis of novel amino acids effective in regulating human metabolism or neurotransmission, as well as food and pharmaceutical compositions utilizing them, are continuously being conducted.

[0010] Meanwhile, protein hydrolysis, fermentation, and chemical synthesis processes are known methods for producing amino acids. The first amino acid produced industrially was glutamic acid. Glutamic acid is produced through a microbial fermentation process using sugars such as glucose, sugarcane, and starch as a raw material for monosodium glutamate (MSG).

[0011] However, existing methods for producing amino acids using microbial fermentation had problems such as high costs, low microbial stability, and unsuitability for mass production due to the complex processes involved, including culture, filtration, and purification. Prior art literature

[0012] Korean Patent Publication No. 10-2024-0046412, Korean Patent Registration No. 10-2620905 The problem to be solved

[0013] The problem that the present invention aims to solve is to provide a novel amino acid derivative.

[0014] Another technical objective of the present invention is to provide a method for producing amino acid derivatives capable of introducing various substituents through a simple chemical reaction. means of solving the problem

[0015] One aspect of the present invention provides an amino acid derivative represented by the following chemical formula (3):

[0016] (3)

[0017] In the above chemical formula (3), R is selected from hydrogen, hydroxyl, C1 to C12 alkyl groups, C1 to C12 alkoxy groups, C2 to C12 alkenyl groups, C1 to C12 alkylamine groups, and C3 to C12 cycloalkyl groups.

[0018] According to the examples, the R may be selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl group, nonyl, decyl, undecyl, and dodecyl, but is not limited thereto.

[0019] Another aspect of the present invention provides a method for producing an amino acid derivative according to the following reaction formula 1, comprising the steps of: adding a basic substance to a solution containing a compound of the following formula (G2); and producing an amino acid derivative of the following formula (3) by changing the pH of the solution due to the basic substance.

[0020] [Reaction Equation 1]

[0021]

[0022] In the above reaction scheme, R is selected from hydrogen, hydroxyl, C1 to C12 alkyl group, C1 to C12 alkoxy group, C2 to C12 alkenyl, C1 to C12 alkylamine group, C3 to C12 cycloalkyl group, and M is a metal ion or ammonium ion.

[0023] According to the example, the solution containing the compound of the chemical formula (G2) may be an aqueous solution, for example, an ultrapure water solution.

[0024] According to the examples, the basic substance may be selected from one or more of sodium oxide, calcium hydroxide, potassium hydroxide, and ammonium hydroxide, but is not limited thereto.

[0025] According to the examples, it is preferable that the reaction be carried out in the range of pH 7 to 11.

[0026] According to the example, the reaction can be carried out in a temperature range of room temperature to 50°C. Effects of the invention

[0027] According to the present invention, a novel amino acid derivative having efficacy similar to glutamic acid or glutamine derived from natural products can be produced by a chemical synthesis method.

[0028] The present invention has the advantage of low manufacturing costs, mass production, and high production efficiency because it can produce amino acid derivatives in high yield under mild conditions through a simple process of adding a basic substance to a solution in which a glutamine compound is dissolved to change the pH.

[0029] Furthermore, since this invention is a chemical synthesis method, various substituents can be introduced into the chemical structure, making it highly applicable to food, cosmetics, pharmaceuticals, and the like.

[0030] The novel amino acid derivative according to the present invention is a type of glutamine derivative. Glutamine is known to have the effect of reducing stress by influencing the release of neurotransmitters in brain nerve cells, and it has the effect of relieving tension and anxiety and lowering stress responses by contributing to an increase in alpha (α) waves in the brain or reducing the secretion of cortisol (stress hormone), thereby exhibiting sedative and stabilizing effects. The amino acid compound according to the present invention is an amino acid derivative with a chemical structure similar to glutamine and exhibits equivalent efficacy to the above, so it can replace conventional glutamine derivatives in manufacturing processes for food, cosmetics, or pharmaceutical compositions.

[0031] The effects of the present invention are not limited to those mentioned above, and other unmentioned effects will be clearly understood by those skilled in the art from the description below. Brief explanation of the drawing

[0032] Figure 1 is the result of mass spectrum analysis of a compound (3a) synthesized according to an example. Specific details for implementing the invention

[0033] The present invention will be described in more detail below with reference to examples and chemical reaction equations. However, the following examples are provided as examples to aid in understanding the invention and do not limit the scope of the invention. The present invention may be modified in various ways and embodied in various different forms, and it should be understood that it includes all modifications, equivalents, and substitutions that fall within the spirit and technical scope of the invention.

[0034] Furthermore, unless otherwise defined, all terms used herein, including technical or scientific terms, have the same meaning as generally understood by those skilled in the art to which the present invention pertains. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant technology, and should not be interpreted in an ideal or overly formal sense unless explicitly defined in this application.

[0035] The amino acid derivative according to an embodiment of the present invention is a compound represented by the following chemical formula (3).

[0036] (3)

[0037] In the above chemical formula (3), R can be selected from hydrogen, hydroxyl, C1 to C12 alkyl groups, C1 to C12 alkoxy groups, C2 to C12 alkenyl groups, C1 to C12 alkylamine groups, and C3 to C12 cycloalkyl groups.

[0038] The above C1 to C12 alkyl groups include both straight-chain and branched-chain alkyl groups, and specific examples may be selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, nonyl, decyl, undecyl, and dodecyl, but are not limited thereto.

[0039] The alkoxy groups of C1 to C12 above include both straight-chain and branched-chain alkoxy groups, and specific examples may be selected from methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, and n-decyloxy, but are not limited thereto.

[0040] Specific examples of the alkenyl groups of the above C2 to C12 may be selected from the group consisting of methenyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl, but are not limited thereto.

[0041] Specific examples of the above C1 to C12 alkylamine groups may be selected from methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, and dodecylamine, but are not limited thereto.

[0042] Specific examples of the above C3 to C12 cycloalkyl groups may be one or more selected from cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, cycloonedecyl group, and cyclododecyl group, but are not limited thereto.

[0043] A method for preparing an amino acid derivative according to the following reaction formula 1 comprises the steps of: adding a basic substance to a solution containing a compound of the following formula (G2); and producing an amino acid derivative of the following formula (3) by changing the pH of the solution due to the basic substance.

[0044] [Reaction Equation 1]

[0045]

[0046] In the above reaction scheme, R is selected from hydrogen, hydroxyl, C1 to C12 alkyl group, C1 to C12 alkoxy group, C2 to C12 alkenyl, C1 to C12 alkylamine group, C3 to C12 cycloalkyl group, and M is a metal ion or ammonium ion.

[0047] The solution containing the compound of the above chemical formula (G2) may be an aqueous solution, for example, an ultrapure water solution.

[0048] The basic substance added to the above reaction may be selected from one or more of sodium hydroxide, calcium hydroxide, potassium hydroxide, and ammonium hydroxide, but is not limited thereto. In order to increase the miscibility and reactivity with the aqueous solution in which the reaction material is dissolved, it is preferable to add a basic substance such as sodium hydroxide in solution form.

[0049] Compound (3) can be synthesized by adding the above basic substance to a solution containing the chemical formula (G2) to adjust the pH to a range of 7 to 11. Under acidic conditions of pH 7 or lower and conditions exceeding pH 11, there is a problem with the structural stability of the compound and it may decompose.

[0050] At this time, the reaction temperature may be in the range of room temperature to 50℃, but it is preferable to perform it at room temperature considering energy efficiency.

[0051] As such, the present invention has the advantage of low manufacturing costs and high production efficiency because it enables the production of amino acid derivatives with high yield under mild conditions through a simple process of dissolving a glutamine compound in a solution (such as water) and then adding a basic substance to change the pH. Furthermore, since the present invention is a chemical synthesis method, various substituents can be introduced into the chemical structure, thus offering high applicability.

[0052] The method for preparing novel amino acid derivatives is explained in more detail through the following examples. However, the following examples are described illustratively to aid in understanding the present invention and should not be interpreted as limiting the scope of the present invention.

[0054] Example 1: Synthesis of an amino acid derivative of formula (3a)

[0055] [Reaction Equation 2]

[0056]

[0057] A glutamine derivative of formula (3a) was synthesized according to reaction scheme 2 above. A 0.1% (w / v) solution was prepared by adding 100 mL of a solution adjusted to pH 7 to 11 using sodium hydroxide to 100 mg of the compound of formula (G2a), and the solution was stirred at room temperature for 1 hour to obtain compound (3a). The yield of the compound (3a) synthesized in this way was 24%.

[0058] To confirm the novel amino acid derivative compound (3a) synthesized through the above reaction, it was analyzed using ultra-high performance liquid chromatography (Agilent, USA) and high-resolution mass spectrometry (Agilent, USA). A C18 column was used as the stationary phase column, and water and methanol containing 1 volume% (v / v) of trifluoroacetic acid were used as the mobile phase solvents. The experiment was performed at a flow rate of 0.5 mL / min and a wavelength of 210 nm.

[0059] As a result of analyzing the substance synthesized in Example 1 using a high-resolution mass spectrometer, compound (3a) of FIG. 1 was identified. Compound (3a) is a novel compound and is a glutamine derivative, which is a type of amino acid.

[0061] Example 2: Synthesis of an amino acid derivative of formula (3b)

[0062] [Reaction Equation 3]

[0063]

[0064] Compound (3b) was synthesized in the same manner as in Example 1 according to the above reaction scheme 3. The yield of the compound (3b) synthesized in this way was 24%.

[0066] Example 3: Synthesis of an amino acid derivative of formula (3c)

[0067] [Reaction Equation 4]

[0068]

[0069] Compound (3c) was synthesized in the same manner as in Example 1 according to the above reaction scheme 4. The yield of the compound (3c) synthesized in this way was 24%.

[0071] Example 4: Synthesis of an amino acid derivative of formula (3d)

[0072] [Reaction Equation 5]

[0073]

[0074] Compound (3d) was synthesized in the same manner as in Example 1 according to the above reaction scheme 5. The yield of the compound (3d) synthesized in this way was 24%.

[0076] Example 5: Synthesis of an amino acid derivative of formula (3e)

[0077] [Reaction Equation 6]

[0078]

[0079] Compound (3e) was synthesized in the same manner as in Example 1 according to the above reaction scheme 6. The yield of the compound (3e) synthesized in this way was 24%.

[0081] Example 6: Synthesis of an amino acid derivative of formula (3f)

[0082] [Reaction Equation 7]

[0083]

[0084] Compound (3f) was synthesized in the same manner as in Example 1 according to the above reaction scheme 7. The yield of the compound (3f) synthesized in this way was 24%.

[0086] Example 7: Synthesis of an amino acid derivative of formula (3g)

[0087] [Reaction Equation 8]

[0088]

[0089] Compound (3g) was synthesized in the same manner as in Example 1 according to the above reaction scheme 8. The yield of the compound (3g) synthesized in this way was 24%.

[0091] Example 8: Synthesis of an amino acid derivative of formula (3h)

[0092] [Reaction Equation 9]

[0093]

[0094] Compound (3h) was synthesized in the same manner as in Example 1 according to the above reaction scheme 9. The yield of the compound (3h) synthesized in this way was 24%.

[0096] Example 9: Synthesis of an amino acid derivative of formula (3i)

[0097] [Reaction Equation 10]

[0098]

[0099] Compound (3i) was synthesized in the same manner as in Example 1 according to the above reaction scheme 10. The yield of the compound (3i) synthesized in this way was 24%.

[0101] Example 10: Synthesis of an amino acid derivative of formula (3j)

[0102] [Reaction Equation 11]

[0103]

[0104] Compound (3j) was synthesized in the same manner as in Example 1 according to the above reaction scheme 11. The yield of the compound (3j) synthesized in this way was 24%.

[0106] Example 11: Synthesis of an amino acid derivative of formula (3k)

[0107] [Reaction Equation 12]

[0108]

[0109] Compound (3k) was synthesized in the same manner as in Example 1 according to the above reaction scheme 12. The yield of the compound (3k) synthesized in this way was 24%.

[0111] Example 12: Synthesis of an amino acid derivative of formula (3l)

[0112] [Reaction Equation 13]

[0113]

[0114] Compound (3l) was synthesized in the same manner as in Example 1 according to the above reaction scheme 13. The yield of the compound (3l) synthesized in this way was 24%.

[0116] Example 13: Synthesis of an amino acid derivative of formula (3m)

[0117] [Reaction Equation 14]

[0118]

[0119] Compound (3m) was synthesized in the same manner as in Example 1 according to the above reaction scheme 14. The yield of the compound (3m) synthesized in this way was 24%.

[0120] Through the above examples, it was confirmed that a novel amino acid derivative represented by the above chemical formula (3) can be produced with high yield under mild conditions through a simple process of dissolving a glutamine compound in an aqueous solution and then adding a basic substance to change the pH. In particular, the method for producing an amino acid derivative according to the embodiments of the present invention can produce glutamine derivatives with various substituents introduced for the intended use through chemical reactions, and thus has high utility because the manufacturing process is simpler and more accurate compared to conventional microbial fermentation processes.

[0121] Although the invention has been described above with reference to embodiments, this is merely illustrative and does not limit the invention. Those skilled in the art will understand that various modifications and applications not exemplified above are possible within the scope of the essential characteristics of the embodiments. For example, each component specifically shown in the embodiments may be modified and implemented. Furthermore, differences related to such modifications and applications should be interpreted as being included within the scope of the invention as defined in the appended claims.

Claims

Claim 1 Amino acid derivatives represented by the following chemical formula (3): (3) In the above chemical formula (3), R is selected from hydrogen, hydroxyl, C1 to C12 alkyl group, C1 to C12 alkoxy group, C2 to C12 alkenyl group, C1 to C12 alkylamine group, C3 to C12 cycloalkyl group. Claim 2 In claim 1, the above R is an amino acid derivative selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, nonyl, decyl, undecyl, and dodecyl. Claim 3 A method for preparing an amino acid derivative according to the following reaction formula 1, comprising the steps of: adding a basic substance to a solution containing a compound of the following formula (G2); and generating an amino acid derivative of the following formula (3) by a change in pH of the solution caused by the basic substance: [Reaction Formula 1] In the above reaction scheme, R is selected from hydrogen, hydroxyl, C1 to C12 alkyl group, C1 to C12 alkoxy group, C2 to C12 alkenyl, C1 to C12 alkylamine group, C3 to C12 cycloalkyl group, and M is a metal ion or ammonium ion. Claim 4 A method for preparing an amino acid derivative according to claim 3, wherein R is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl group, nonyl, decyl, undecyl, and dodecyl. Claim 5 In paragraph 3, a method for preparing an amino acid derivative in which the solution containing the compound of the chemical formula (G2) is an aqueous solution. Claim 6 A method for preparing an amino acid derivative in which, in paragraph 3, the basic substance is one or more selected from sodium hydroxide, calcium hydroxide, potassium hydroxide, and ammonium hydroxide. Claim 7 A method for preparing an amino acid derivative according to claim 3, wherein the reaction is performed in the range of pH 7 to 11. Claim 8 In paragraph 3, the method for preparing an amino acid derivative wherein the reaction is performed at room temperature to 50°C.

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