Compounding method for glutathione

A technology of glutathione and synthesis method, applied in the field of cosmetics and medicine, can solve the problems of unfriendly environment, high cost of chemical synthesis method, high toxicity of raw materials, etc., and achieve the effects of reducing cost, high purity and improving yield

Inactive Publication Date: 2018-01-12
HUBEI HUNTIDE BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0027] In order to solve the problems of high cost of chemical synthesis, high toxicity of raw materials used and unfriendly to the environment, the method provided by the present invention has the advantages of simple and easy-to-obtain raw materials, mild process conditions and high reaction yield. The steps of the synthetic method are as follows:

Method used

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  • Compounding method for glutathione
  • Compounding method for glutathione
  • Compounding method for glutathione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of Cystyl Chloride Phthalic Anhydride

[0050] In a 500mL reaction flask, add 120mL of toluene, 24g (0.1mol) of L-cystine, and 44.4g (0.3mol) of phthalic anhydride, then raise the temperature to 110°C, separate the water, and monitor the completion of the reaction by HPLC after the reaction solution is dissolved. Solids were precipitated, filtered, the filter cake was washed with 100ml of methanol, and dried to obtain 43.5g of cystine phthalic anhydride, with a yield of 86.9%.

[0051] Put 43.5g (0.086mol) of cystine phthalic anhydride into 150ml of chloroform, add 40.9g (0.344mol) of thionyl chloride dropwise, then raise the temperature to about 75°C and reflux for about 4 hours. After the reaction is dissolved, sample the derivative methyl ester for HPLC monitoring. After the reaction is complete, concentrate the net chloroform and excess thionyl chloride, and then add 150ml of chloroform to the oil for later use.

Embodiment 2

[0052] Embodiment 2: Preparation of glutathione

[0053] Add glycine 19.3g (0.258mol), toluene 20ml, HMDS 83.3g (0.516mol) into a 250mL reaction bottle, heat up to 110°C for reflux reaction for 2 hours, the reaction is complete after dissolution, it is glycine protected by HMDS, Cool down to 15°C for later use. Add the acid chloride in Example 1 dropwise into the HMDS-protected glycine, keep the temperature between 10-20°C to react, and react overnight after dropping, HPLC detects that the acid chloride has completely reacted, concentrated the solvent under reduced pressure, then added 200ml of water and stirred, and a large amount of solids Precipitated, filtered to obtain phtalic anhydride glutathione, and dried to obtain 43.9g with a purity of 94.7%.

[0054] In a 500ml reaction bottle, put 43.9g (0.068mol) of phtalic anhydride glutathione into 150ml of water, then add 7.6g (0.205mol) of 85% hydrazine hydrate, heat up to 70°C, react for 4h to sample HPLC raw materials, and...

Embodiment 3

[0055] Embodiment 3: tripeptide preparation

[0056] In a 1000mL reaction flask, add 64g (0.435mol) of glutamic acid, 300ml of toluene, and 96.5g (0.652mol) of phthalic anhydride, raise the temperature to about 110°C for reflux reaction, divide water, and monitor the reaction by HPLC after about 3 hours for the reaction solution to dissolve. After cooling down, solids were precipitated, filtered, the filter cake was washed with 120ml of methanol, and dried to obtain 98.8g of phthalic anhydride glutamic acid. In a 500ml reaction bottle, put 98.8g (0.357mol) of phthalic anhydride glutamic acid, then add 291.3g (2.85mol) of acetic anhydride, heat up to reflux, after 2 hours of reaction, TLC shows that the raw materials are completely reacted, cool down and filter, and use 100ml of ethyl acetate The ester was washed and dried to obtain 80.3 g (0.309 mol) of phthalic anhydride and glutamic anhydride.

[0057] In another 500ml reaction bottle, add 22.7g (0.064mol) of glutathione di...

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Abstract

The invention discloses a compounding method for glutathione and belongs to the technical field of cosmetics and medicines. The method comprises the following steps: protecting L-cystine with phthalicanhydride (called as phthalic anhydride for short); preparing acyl chloride and condensing acyl chloride with glycine protected with hexamethyldisilazane (called as HMDS for short), thereby acquiringcysteine glycine dipeptide protected with phthalic anhydride; removing the phthalic anhydride protecting group, thereby acquiring the cysteine glycine dipeptide; protecting glutamic acid with phthalic anhydride and then reacting with acetic anhydride, thereby acquiring anhydride anhydride; reacting with cysteine glycine dipeptide, thereby acquiring tripeptide; and removing phthalic anhydride protection, thereby acquiring oxidized glutathione, and then reducing S-S bond, thereby acquiring the reduced glutathione GSH. According to the method, a chemical synthesis method is adopted for synthesizing the oxidized and reduced glutathione, the raw materials are low in cost, the yield is high, the high-purity products can be acquired and the method can meet the requirement for industrial production.

Description

technical field [0001] The invention relates to the technical fields of cosmetics and medicine, in particular to a method for synthesizing glutathione, in particular to a method for synthesizing reduced glutathione. Background technique [0002] The English name of L-glutathione is Glutathione, abbreviated as reduced GSH, which is a white crystalline solid with the following structure: [0003] [0004] Reduced glutathione has been proven to be mainly related to cell differentiation, animal growth and maintenance of systemic antioxidant function, especially closely related to liver tissue differentiation and maintenance of normal function. It is widely used in clinical medicine, food industry, Cosmetics, sports and other biological research fields. Reduced glutathione is a small molecule peptide that exists in large quantities in living organisms, especially in liver cells. It can protect liver cell membranes, promote the activity of liver enzymes, and combine with many ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/037C07K1/06C07K1/02
CPCY02P20/55
Inventor 黄发勋张锐雷玉平吴伟伟鲍汝杨汪黎明李健雄
Owner HUBEI HUNTIDE BIOTECH
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