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Synthesis process of gamma-L-glutamine-cysteine

A technology of cysteine ​​and synthesis method, which is applied in the field of chemical synthesis, can solve the problems of difficult repeatability of experiments and low yield, and achieve the effects of good selectivity, high yield and low production cost

Inactive Publication Date: 2007-08-29
NANJING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Currently, there are few methods for preparing γ-GC, only Harington et al. [Harington, C.A.; After L-cystine ethyl ester is condensed, N-benzyloxy-γ-L glutamyl-L-cystine is obtained by zinc powder reduction and saponification reaction, which is reduced to γ-GC with phosphorus iodide in glacial acetic acid , the yield is low and the experiment is not easy to repeat

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 147 grams of L-glutamic acid and 148 grams of phthalic anhydride into a 500ml flask, control the temperature of the oil bath at 150±5°C, react for 45 minutes after melting, pour it into boiling water while it is hot, cool and crystallize to obtain phthalic acid Acyl-L-glutamic acid 224.4 grams (yield 81%); Phthalyl-L-glutamic acid 55.4 grams boiled in acetic acid for 5 minutes to produce phthalyl-L-glutamic anhydride 46.6 grams ( Yield 90%); 31.0 grams of this acid anhydride is reacted with 12.0 grams of L-cystine, 4.0 grams of sodium hydroxide, and 100 ml of water solution at room temperature, and the pH of the reaction solution is maintained at 8 to 10 by dropping 10 wt % sodium carbonate solution, Obtain 30.3 grams of diphthalyl-γ-L-glutamyl-L-cystine (yield 80%) with the hydrochloric acid acidification of 6 mol / L after 8 hours; Diphthalyl-γ - 22.7 grams of L-glutamyl-L-cystine was directly dissolved in 150 ml of 3% hydrazine hydrate aqueous solution at room temp...

Embodiment 2

[0031] The preparation method of phthaloyl-L-glutamic anhydride is the same as that in Example 1. 31.0 grams of this anhydride is reacted with 12.0 grams of cystine, 10.6 grams of sodium carbonate, and 100 ml of water solution at room temperature, and the solution is added dropwise with 10 mol / L sodium hydroxide solution maintained reaction solution pH 8~10, obtained 31.1 grams of diphthaloyl-γ-L-glutamyl-L-cystine with 6 mol / L sulfuric acid acidification after 8 hours (yield 83 %); Following steps are with embodiment 1, obtain 9.7 gram gamma-GC (total yield 47%).

Embodiment 3

[0033] Synthesize diphthalyl-γ-L-glutamyl-L-cystine with the same operation steps as in Example 2; weigh diphthalyl-γ-L-glutamyl-L-cystine 16 grams of amino acid were directly dissolved in 100 ml of 3% hydrazine hydrate in water and ethanol solution at room temperature and placed for two days, acidified with 6mol / L formic acid, adjusted to pH 3, filtered to remove the phthalylhydrazide precipitate, and the filtrate was reduced Concentrate under pressure, add dropwise 4mol / L sodium hydroxide solution to adjust pH to 6.0, separate out γ-L-glutamyl-L-cystine 8.9 grams (yield 88%) with 95% ethanol; Same with embodiment 1 Operation steps Preparation of γ-GC (total yield 48%).

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Abstract

The present invention discloses the synthesis process of gamma-L-glutamyl-L-cysteine (gamma-GC). The synthesis process includes the following steps: reaction between phthalic anhydride and L-glutamic acid at 120-180 deg.c to produce phthalyl-L-glutamic acid, azeotropic reaction with acetic acid for 3-20 min to form phthalyl-L-glutamic anhydride, direction reaction with L-cystine sodium aqua at room temperature to produce diphthalyl-gamma-L-glutamyl-L-cystine, adding into solution of hydrazine hydrate and setting for 2 days to eliminate protective radical to gamma-L-glutamyl-L-cystine, and electrolytically reduction to prepare amma-L-glutamyl-L-cysteine. The synthesis process has the advantages of low material cost, low production cost, fast reaction speed, high selectivity, high yield, etc.

Description

1. Technical field [0001] The invention relates to a synthesis method of gamma-L-glutamyl-L-cystine (gamma-GC), belonging to the field of chemical synthesis. 2. Technical background [0002] γ-L-aminoacyl-L-cystine can be used as a food additive for improving the taste of food [Chinese patent CN 1550157A], and it is also an important precursor for the biosynthesis of reduced glutathione (glutathione). Reduced glutathione is a small molecule free radical scavenger that can scavenge O 2 、H 2 o 2 . It is a small molecular peptide composed of glutamic acid, cysteine, and glycine. It is the main non-protein sulfhydryl compound in tissues and the substrate of various enzymes. It can stabilize sulfhydryl-containing enzymes and prevent hemoglobin Self and other cofactors are subject to oxidative damage. It also plays an important role in the treatment of diseases such as arteriosclerosis, coronary heart disease, anti-aging, anti-tumor and Alzheimer's disease. [0003] Although...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/00C07C237/00
Inventor 焦庆才钱绍松王先斌曾庆群陈然肖国安
Owner NANJING UNIV
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