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Synthetic method of trifluoroacetyl tripeptide-2

A technology of trifluoroacetyl tripeptide and synthesis method, which is applied in the field of cosmetics, can solve the problems of high synthesis cost, low efficiency, and complicated process, and achieve the effect of low synthesis cost, high efficiency, and simple process

Active Publication Date: 2018-03-30
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 synthetic method of trifluoroacetyl tripeptide-2. According to the synthetic method, NH2-Val-Tyr(tBu)-Val-Wang Resin resin peptide is synthesized firstly through Wang Resin,then resin peptide is reacted with 6-chlorobenzotriazole-1,1,3,3-tetramethylurea hexafluorophophate, 1-hydroxybenzotriazole, trifluoroacetic acid and N, N'-diisopropylethylamine to synthesize N-(2,2,2-trifluoroacetyl)-Val-Tyr(tBu)-Val-Wang Resin, finally cutting treatment, purification and freeze drying are conducted on N-(2,2,2-trifluoroacetyl)-Val-Tyr(tBu)-Val-Wang Resin, and thus trifluoroacetyl ripeptide-2 is obtained. According to the synthetic method, trifluoroacetic acid which is low in cost and easy to get is adopted to replace trifluoroacetic acid ethyl ester or trifluoro-acetic chloride which is relatively high in cost, meanwhile, the technology that trifluoroacetic acid is activated in firstly and then acidity is neutralized is adopted, the influence of trifluoroacetic acid toNH2-Val-Tyr(bTu)-Val-Wang Resin is overcome, the synthetic method has the advantages of being low in cost, high in efficiency and simple in method, and is an ideal synthetic method of trifluoroacetyltripeptide-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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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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