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Synthesis method for GHK tripeptide

A synthetic method, the technology of -OH, is applied in the field of synthesizing GHK tripeptide to achieve simple operation steps, help separation and purification, and increase lipophilicity

Active Publication Date: 2014-03-26
SHAANXI HUIKANG BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of existing GHK tripeptide preparation methods, and provide a synthesis method of GHK tripeptide with simple operation, low cost and easy separation and purification of products

Method used

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  • Synthesis method for GHK tripeptide
  • Synthesis method for GHK tripeptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. Synthesis of H-Lys(Ac)-OH

[0026] Add 10g (0.07mol) lysine and 40mL distilled water into the reaction flask, stir at room temperature, adjust the pH value to 10 with 10% sodium hydroxide aqueous solution, and slowly add 15.2g (0.08mol) p-nitrobenzene acetate The mixture of ester (provided by Shanghai Puzhen Biotechnology Co., Ltd.) and 80mL 1,4-dioxane was stirred at room temperature for 4 hours, filtered, the filtrate was concentrated under reduced pressure, extracted with ethyl acetate, and the aqueous phase was used with a mass fraction of 10% citric acid aqueous solution adjusted the pH value to 3, extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate and filtered under reduced pressure, the filtrate was concentrated to dryness under reduced pressure to obtain H-Lys(Ac)-OH, the yield 96%.

[0027] 2. Synthesis of Boc-Gly-COOSu

[0028] Add 10g (0.057mol) Boc-Gly-OH and 100mL 1,4-dioxane into the reaction flask, stir at room te...

Embodiment 2

[0039] In step 1 of the synthesis of H-Lys(Ac)-OH in this example, add 10 g (0.07 mol) of lysine and 40 mL of distilled water into the reaction flask, stir at room temperature, and adjust the pH with 10% sodium hydroxide aqueous solution value to 11, slowly add a mixture of 26.6g (0.0.14mol) p-nitrophenyl acetate (provided by Shanghai Puzhen Biotechnology Co., Ltd.) and 250mL 1,4-dioxane, and stir at room temperature for 5 hours. The other steps of the steps are the same as in Example 1 to obtain H-Lys(Ac)-OH. The other steps were the same as in Example 1 to obtain the GHK tripeptide.

Embodiment 3

[0041] In step 3 of the synthesis of Boc-Gly-His(Boc)-OH in this example, 17.8g (0.0.114mol) of histidine and 9.6g (0.114mol) of sodium bicarbonate were dissolved in 30mL of distilled water, and the resulting solution was added dropwise Into the 1,4-dioxane solution of Boc-Gly-COOSu obtained in step 2, stirred at room temperature for 20 hours, then added dropwise 24.6g (0.114mol) of di-tert-butyl dicarbonate and 200mL of 1,4-dioxane Add 9.3 g (0.228 mol) of sodium hydroxide to the hexacyclic mixture, and react at room temperature for 3 hours. Other steps in this step are the same as in Example 1 to obtain Boc-Gly-His(Boc)-OH. The other steps were the same as in Example 1 to obtain the GHK tripeptide.

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Abstract

The invention discloses a synthesis method for GHK tripeptide. A conventional liquid-phase synthesis method is adopted. The method comprises the following steps of protecting lysine by using p-nitrophenyl acetate, protecting dipeptide obtained by enabling Boc-Gly-OH to react with histidine by using di-tert-butyl dicarbonate, and enabling the protected dipeptide to react with the protected lysine to obtain the GHK tripeptide. According to the method, the p-nitrophenyl acetate is used for protecting the lysine, and can selectively acylate amino groups farther away from carboxylic acid functional groups, and compared with a conventional protecting method, the p-nitrophenyl acetate protecting method has the advantages that the operating steps are simple, and the production cost is lowered; the di-tert-butyl dicarbonate is used for protecting the dipepetide, so that the generation of other byproducts is reduced, the lipophicity of a chemical compound is improved, the separation and purification of a product are facilitated, the yield of the product is improved, and meanwhile, the generation of a recemization product can also be reduced.

Description

technical field [0001] The invention belongs to the technical field of cosmetics, and in particular relates to a method for synthesizing GHK tripeptide by means of liquid phase. Background technique [0002] GHK tripeptide is an active polypeptide containing three amino acids. The amino acid sequence is H-Gly-His-Lys-OH. GHK-Cu was first used in medicine to promote wound healing and improve skin elasticity. Some recent studies believe that it can improve For fine lines, PAL-GHK has the effect of plumping lips. It is used in the production of lipsticks. After use, it makes lips look plump and soft, with a unique lip scene. It is also an essential raw material for safe breast enhancement products. [0003] At present, the synthesis method of GHK mainly adopts classical solid-phase synthesis. Solid-phase synthesis involves extending the protected amino acids from the C-terminus to the N-terminus one by one. GHK products with a purity higher than 90% are prepared through conden...

Claims

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Application Information

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IPC IPC(8): C07K5/083C07K1/06C07K1/02
Inventor 刘林张腾宋卫刘晓芸张忠旗杨晓琳赵金礼
Owner SHAANXI HUIKANG BIO TECH CO LTD
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