A kind of synthetic method of trifluoroacetyl tripeptide-2

The technology of a trifluoroacetyl tripeptide and a synthesis method, which is applied in the field of cosmetics, can solve the problems of high synthesis cost, complex process and low efficiency, and achieve the effects of low synthesis cost, simple process and high efficiency

Active Publication Date: 2021-05-04
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 the existing trifluoroacetyl tripeptide-2 synthesis cost, low efficiency and complicated process, and provide a solid trifluoroacetyl tripeptide-2 with low cost, high efficiency and simple synthesis process. phase synthesis method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Synthesis of NH 2 -Val-Tyr(tBu)-Val-Wang Resin

[0028] ①Synthesis of Fmoc-Val-Wang Resin

[0029] Add 20.0g Wang Resin (substitution degree 0.5mmol / g) into the synthesizer, add 200mL N,N-dimethylformamide and soak for 4 hours to make it fully swell, and remove N,N-dimethylformamide by suction filtration , add 200mL dichloromethane, 33.94g Fmoc-Val-OH, 1.22g 4-dimethylaminopyridine, 7.79mL N,N-diisopropylcarbodiimide, Wanggresin and Fmoc-Val-OH to the synthesizer , 4-dimethylaminopyridine, N,N-diisopropylcarbodiimide in a molar ratio of 1:10:1:5, under nitrogen protection, stirred and reacted at room temperature for 4 hours, filtered with suction, and used isopropanol and N,N-Dimethylformamide was washed twice, 180 mL each time, to obtain Fmoc-Val-Wang Resin.

[0030] ②Synthesis of Fmoc-Tyr(tBu)-Val-Wang Resin

[0031] Add the Fmoc-Val-Wang Resin obtained in step ① into the synthesizer, and add 200mL of a mixture of piperidine and N,N-dimethylformamide with a vo...

Embodiment 2

[0041] In ② and ③ of step (1) of this embodiment, the molar ratio of 1-hydroxybenzotriazole, N,N-diisopropylcarbodiimide to Wanggresin is 2.5:2.5:1, other steps of this step Same as Example 1. In step (2) of this implementation, 6-chlorobenzotriazole-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-hydroxybenzotriazole, trifluoroacetic acid and Wang resin Molar ratio is 3:3:2:1, and other steps of this step are identical with embodiment 1. The step (3) of this implementation is the same as in Example 1 to obtain 3.6 g of trifluoroacetyl tripeptide-2 lyophilized powder, with a yield of 74.00%.

Embodiment 3

[0043] In step (2) of this implementation, 6-chlorobenzotriazole-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-hydroxybenzotriazole, trifluoroacetic acid and Wang resin Molar ratio is 5:5:4:1, and other steps of this step are identical with embodiment 1. Steps (1) and (3) of this implementation are the same as in Example 1, and 4.1 g of trifluoroacetyl tripeptide-2 freeze-dried powder is obtained with a yield of 84.25%.

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Abstract

The invention discloses a method for synthesizing trifluoroacetyl tripeptide-2. The method first synthesizes NH by Wang Resin 2 ‑Val‑Tyr(tBu)‑Val‑Wang Resin resin peptide, and then the resin peptide and 6‑chlorobenzotriazole‑1,1,3,3‑tetramethyluronium hexafluorophosphate, 1‑hydroxy Synthesis of N-(2,2,2-trifluoroacetyl)-Val-Tyr(tBu)-Val-Wang Resin by reaction of benzotriazole, trifluoroacetic acid and N,N′-diisopropylethylamine, and finally It was cut, purified, and freeze-dried to obtain trifluoroacetyl tripeptide-2. The present invention adopts low-cost, simple and easy-to-obtain trifluoroacetic acid to replace expensive ethyl trifluoroacetate or trifluoroacetyl chloride, and simultaneously adopts the process of first activating trifluoroacetic acid and then neutralizing the acidity, thereby overcoming the effect of trifluoroacetic acid on NH 2 The influence of ‑Val‑Tyr(tBu)‑Val‑Wang Resin resin peptide has the advantages of low cost, high efficiency and simple method, and is an ideal method for the synthesis of trifluoroacetyl tripeptide‑2.

Description

technical field [0001] The invention belongs to the technical field of cosmetics, and in particular relates to a synthesis method of trifluoroacetyl tripeptide-2. Background technique [0002] Trifluoroacetyl tripeptide-2 is an active polypeptide composed of three amino acids, its sequence is N-(2,2,2-trifluoroacetyl)-Val-Tyr-Val-OH, this polypeptide can inhibit MMP -1 stimulates the production of ECM for anti-wrinkle and anti-aging. Therefore, it is mostly used in cosmetics as a matrix care element. [0003] At present, the disadvantages of the synthesis of trifluoroacetyl tripeptide-2 are mainly that ethyl trifluoroacetate or trifluoroacetyl chloride is often used as an acylating reagent during trifluoroacetylation, which has high material cost, low efficiency, and complicated synthesis process. Trifluoroacetyl tripeptide-2 is used as a raw material for cosmetics, so it is of great significance to reduce production costs, improve production efficiency, and simplify the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/083C07K1/06C07K1/04
CPCC07K5/0808
Inventor 李乾张忠旗郭添张佳旭范永刚王慧张博杨小琳赵金礼
Owner SHAANXI HUIKANG BIO TECH CO LTD
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