Method for synthesizing reduced glutathione

A technology of glutathione and synthesis method, applied in the field of amino acid tripeptide chemical synthesis

Inactive Publication Date: 2011-06-15
天津市利发隆化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the reaction is completed, the protective group must be removed under high reducing conditions. Therefore, there are many reaction steps, many side reactions, long reaction time, complicated operation, and high cost in the reaction process, which is not conducive to promoting production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A synthetic method for reduced glutathione, comprising the following steps:

[0043] (1) Preparation of CBZ-glutamic acid:

[0044] Put 10g of glutamic acid in a three-neck flask, dissolve it in 60ml of sodium hydroxide solution with a concentration of 1 mol / L, cool it in an ice-salt water bath, slowly add 10.9g of CBZ dropwise under stirring, and continuously add 2 mol / L 1 L of sodium hydroxide solution to maintain the pH of the reaction solution = 9, and the temperature was maintained at 0 °C. After the addition, the temperature was raised to room temperature, and the reaction was continued to stir for 2 h. The reaction was stopped, washed twice with ether, the ether layer was discarded, and washed The solution was extracted with ethyl acetate, the ethyl acetate layer was separated, the aqueous layer was extracted twice with ethyl acetate, the ethyl acetate layers were combined, dried with anhydrous sodium sulfate, and the ethyl acetate was evaporated to obtain a whit...

Embodiment 2

[0060] A synthetic method for reduced glutathione, comprising the following steps:

[0061] (1) Preparation of CBZ-glutamic acid:

[0062] Put 10g of glutamic acid in a three-neck flask, dissolve it in 60ml of sodium hydroxide solution with a concentration of 1 mol / L, cool it in an ice-salt water bath, slowly add 10.9g of CBZ dropwise under stirring, and continuously add 2 mol / L The pH of the reaction solution was maintained at 9.5 with 1 L of sodium hydroxide solution, and the temperature was maintained at 5 °C. After the addition, the temperature was raised to room temperature, and the reaction was continued to stir for 3 h. The solution was extracted with ethyl acetate, the ethyl acetate layer was separated, the aqueous layer was extracted twice with ethyl acetate, the ethyl acetate layers were combined, dried with anhydrous sodium sulfate, and the ethyl acetate was evaporated to obtain a white solid. Add petroleum ether, grind it in an ice bath until it is solid, immediat...

Embodiment 3

[0078] A synthetic method for reduced glutathione, comprising the following steps:

[0079] ⑴, the preparation of CBZ-glutamic acid:

[0080] Put 10g of glutamic acid in a three-neck flask, dissolve it in 60ml of sodium hydroxide solution with a concentration of 1 mol / L, cool it in an ice-salt water bath, slowly add 10.9g of CBZ dropwise under stirring, and continuously add 2 mol / L sodium hydroxide solution to maintain the pH of the reaction solution = 8.5, and the temperature was maintained at 3 °C. After the addition, the temperature was raised to room temperature, and the reaction was continued to stir for 2.5 h. The reaction was stopped, washed twice with ether, and the ether layer was discarded. The lotion was extracted with ethyl acetate, the ethyl acetate layer was separated, the water layer was extracted twice with ethyl acetate, the ethyl acetate layers were combined, dried with anhydrous sodium sulfate, and the ethyl acetate was evaporated to obtain a white solid ,...

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PUM

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Abstract

The invention relates to a method for synthesizing reduced glutathione. The method comprises the following steps of: (1), preparing R-glutamic acid; (2), preparing R-glutamic anhydride; (3), preparing R-glutamic-alpha-benzyl ester; (4), preparing R-glutamic-alpha-benzyl ester-gamma-acyl chloride; (5), preparing R-glutamic-alpha-benzyl ester-cystine; (6) preparing glycine-benzyl ester hydrochloride; (7) preparing bisR-S-S-glutathione-tetrabenzyl ester; and (8), preparing the reduced glutathione. The method has a simple and environmentally-friendly process step; the synthesizing steps are shortened; the yield is improved; and the used raw materials have relatively low cost. The method is the method for synthesizing the reduced glutathione, which has relatively high innovativeness.

Description

technical field [0001] The invention belongs to the field of amino acid tripeptide chemical synthesis, in particular to a method for synthesizing reduced glutathione. Background technique [0002] Reduced glutathione is a tripeptide compound formed by connecting glutamic acid, cysteine, and glycine through peptide bonds, abbreviated as GSH. It contains a lively thiol-SH, which is easily oxidized to generate oxidized glutathione (GSSG). This specific structure enables it to scavenge free radicals in the body. Produce strong protection for the body, thus having the following clinical effects: detoxification, anti-radiation sickness and radiation protection, liver protection, anti-allergy, improvement of the course and symptoms of certain diseases, beauty and skin care, increase vision and treatment of eye diseases, anti-aging . Reduced glutathione preparations have been widely used clinically, and are also widely used in the fields of food and cosmetics, and the market deman...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/093
Inventor 李建发全志利
Owner 天津市利发隆化工科技有限公司
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