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Liquid-phase segmented synthesis method of argireline

A segmented synthesis and hexapeptide technology, which is applied to the preparation method of peptides, chemical instruments and methods, peptides, etc., can solve the problems of excessive reaction reagents, high prices, and many types of solvents.

Active Publication Date: 2014-03-05
SHAANXI HUIKANG BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The market price of the resin required in this method is relatively expensive, and its exchange activity is small, and there are many types of solvents used in the synthesis, and the amount of reaction reagents is obviously excessive, resulting in an increase in the cost of hexapeptide raw materials
As a cosmetic raw material, the current market price of hexapeptide is about 1,000 yuan / g, which makes the finished cosmetics containing hexapeptide expensive and difficult for the general population to accept. Therefore, the research on the process method to reduce the production cost of hexapeptide is of great significance

Method used

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  • Liquid-phase segmented synthesis method of argireline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1. Synthesis of AcOSu

[0039] According to the molar ratio of N-hydroxysuccinimide to diisopropylethylamine and acetyl chloride is 1:1.2:1.1, put 11.5g of N-hydroxysuccinimide in a 250mL three-necked bottle, add 100mL di Chloromethane, mix well, add 20.7mL diisopropylethylamine under stirring condition, cool down to 0~5℃ in ice bath, when the solution becomes clear, add 7.9mL acetyl chloride dropwise, keep the solution temperature below 20°C during the dropwise addition ℃, remove the ice bath after the dropwise addition, naturally rise to room temperature and stir for 3 hours, wash the reaction solution with water 3 times, 50mL each time, dry the organic phase over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 15.3g of AcOSu , the yield is 97.4%.

[0040] 2. Synthesis of Ac-Glu(OtBu)-OH

[0041] According to the molar ratio of AcOSu to γ-tert-butyl glutamic acid and sodium bicarbonate as 1:1.1:2, and the volume ratio of distilled ...

Embodiment 2

[0066] Synthesis of Ac-Glu(OtBu)-OH step 2, Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-OH step 4, Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-OH step in this example 6. In step 9 of the synthesis of Fmoc-Gln(Trt)-Arg-OH, the molar weight of sodium bicarbonate used is 1.5 times that of sodium bicarbonate in Example 1. Other steps are identical with embodiment 1, obtain 6.4g hexapeptide, yield is 90.1%, HPLC detection shows that purity is 90%.

Embodiment 3

[0068] Synthesis of Ac-Glu(OtBu)-OH step 2, Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-OH step 4, Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-OH step in this example 6. In step 9 of synthesizing Fmoc-Gln(Trt)-Arg-OH, the molar weight of sodium bicarbonate used is 3 / 4 of the molar weight of sodium bicarbonate in Example 1. The other steps were the same as in Example 1 to obtain 6.47g hexapeptide with a yield of 91%, and HPLC detection showed that the purity was greater than 90%.

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Abstract

The invention discloses a liquid-phase segmented synthesis method of argireline. The comprises the following steps: respectively synthesizing a tripeptide segment Ac-Glu-(OtBu)-Glu(OtBu)-Met-OH and a dipeptide segment H2N-Gln(Trt)-Arg-OH in an argireline sequence by carrying out segmentation on the argireline sequence, and then synthesizing a pentapeptide segment Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg-OH by a method of taking the tripeptide segment and the dipeptide segment as activated esters; carrying out condensation on the pentapeptide segment and H-Arg-NH2.2HCl, so as to obtain protective hexapeptide Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg-Arg-NH2; and finally carrying out deprotection, so as to obtain the argireline. By adopting the method disclosed by the invention, the defects that protective amino acid must be used by each step in solid-phase reaction, the solvents are diverse in variety and the reagent is obviously excessive and is difficult to recover are overcome. The liquid-phase segmented synthesis method has the advantages of being simple in synthesis method, low in product cost, more environmental to the environment and the like, and can be applied to synthesis of the argireline.

Description

technical field [0001] The invention belongs to the technical field of cosmetics, and in particular relates to a method for synthesizing short peptides in polypeptides. Background technique [0002] Hexapeptide is an active polypeptide containing six amino acids, the amino acid sequence is Ac-Glu-Glu-Met-Gln-Arg-Arg-NH 2 , has the biological activity of skin wrinkle removal, and is widely used in various advanced beauty cosmetics. [0003] At present, the synthesis method of hexapeptide mainly adopts the classic solid-phase method. That is to say, the protected amino acids are extended from the C-terminal to the N-terminal one by one, and the hexapeptide product with a purity higher than 90% is prepared by condensation, deprotection, recondensation, resin cutting, centrifugation, freeze-drying and high-performance liquid phase. The market price of the resin required in this method is relatively expensive, and its exchange activity is small, and there are many types of solv...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/06C07K1/02
Inventor 宋卫刘林张腾韩彬刘晓芸赵金礼杨晓琳
Owner SHAANXI HUIKANG BIO TECH CO LTD
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