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A kind of synthetic method of tetradecylaminobutyryl valinamide butyric acid urea trifluoroacetate

A technology of tetradecylaminobutyryl valinamidobutyric acid urea trifluoroacetate and tetradecylaminoformic acid, which is applied in the field of short peptide synthesis and achieves simple and fast synthesis method, low cost and synthesis efficiency high effect

Active Publication Date: 2021-01-01
SHAANXI HUIKANG BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few reports on the synthetic method of tetradecylaminobutyryl valyl amidobutyric acid urea trifluoroacetate, so the simple and convenient tetradecyl aminobutyryl valyl amido butyric acid urea trifluoroacetate is developed. Acetate Synthesis Method Has Practical Significance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Synthesis of Tetradecylcarbamate

[0023] ①Add 10.67g (0.05mol) of 1-tetradecylamine into 160mL of chloroform, then add 20.8mL (0.15mol) of triethylamine, dissolve until clear, then add 5.0mL (0.0525mol) of chlorine dropwise under stirring The mixed solution of ethyl formate and 20mL chloroform, after the dropwise addition, continue to stir at room temperature for 2 hours. Dry in vacuo to obtain 13.54g of ethyl tetradecylcarbamate (CH 3 (CH 2 ) 12 CH 2 NH-CO-OCH 2 CH 3 ).

[0024] ②Add the ethyl tetradecylcarbamate obtained in step ① into the mixed solution of 270mL tetrahydrofuran and 135mL methanol, stir to dissolve, then add 135mL of 10% lithium hydroxide aqueous solution with a mass concentration of 10% at 0-5°C, and stir to react For 3 hours, use 1 mol / L hydrochloric acid to adjust pH=4~5, remove THF and methanol by rotary evaporation, extract with ethyl acetate (120 mL×3 times), combine ethyl acetate phases, dry with anhydrous sodium sulfate, and rotary...

Embodiment 2

[0033] In ① of step (1) of this embodiment, the molar ratio of 1-tetradecylamine, ethyl chloroformate, and triethylamine is 1:1:2, and the reaction time is 1 hour. ② of step (1) of this embodiment Among them, the reaction time is 2 hours, other steps of this step are identical with embodiment 1, obtain 11.48g tetradecylcarbamic acid, yield 89.20%.

[0034] In ① of step (2) of this embodiment, the reaction time is 1 hour. In ② and ③ of step (2) of this embodiment, 2-CTCResin and Fmoc-Val-OH, Fmoc-DAB(Boc)-OH, ten Tetraalkylcarbamic acid (CH 3 (CH 2 ) 12 CH 2 The molar ratio of NH-COOH) is 1:2, the molar ratio of 2-CTC Resin, 1-hydroxybenzotriazole, and N,N-diisopropylcarbodiimide is 1:2.5:2.5, and the reaction time Be 1.5 hours, other steps of this step are identical with embodiment 1.

[0035] In step (3) of this embodiment, the reaction time is 1 hour, and the other steps of this step are the same as in Example 1 to obtain 8.41 g of tetradecylaminobutyryl valinyl amidobu...

Embodiment 3

[0037] In ① of step (1) of this embodiment, the molar ratio of 1-tetradecylamine, ethyl chloroformate, and triethylamine is 1:1.1:4, and the reaction time is 3 hours. ② of step (1) of this embodiment Among them, the reaction time is 4 hours, other steps of this step are identical with embodiment 1, obtain 12.07g tetradecylcarbamic acid, yield 93.78%.

[0038] In ① of step (2) of this embodiment, the reaction time is 2 hours. In ② and ③ of step (2) of this embodiment, 2-CTCResin and Fmoc-Val-OH, Fmoc-DAB(Boc)-OH, ten Tetraalkylcarbamic acid (CH 3 (CH 2 ) 12 CH 2 The molar ratio of NH-COOH) is 1:2, the molar ratio of 2-CTC Resin, 1-hydroxybenzotriazole, and N,N-diisopropylcarbodiimide is 1:4:4, and the reaction time Be 3 hours, other steps of this step are identical with embodiment 1.

[0039] In step (3) of this embodiment, the reaction time is 2 hours, and the other steps of this step are the same as in Example 1 to obtain 8.57 g of tetradecylaminobutyryl valinyl amidobut...

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Abstract

The invention discloses a synthesis method for tetradecyl aminobutyroylvalylaminobutyric urea trifluoroacetate. With tetradecylamine and ethyl chloroformate as materials, the method synthesizes tetradecylaminoformate by a liquid-phase method; then by a solid-phase synthesis method, with 2-CTC Resin as a solid-phase carrier, Fmoc-DAB(Boc)-OH, Fmoc-Val-OH, Fmoc-DAB(Boc)-OH and the tetradecylaminoformate are sequentially connected to 2-CTC Resin, so that CH3(CH2)12CH2NH-CO-DAB(Boc)-Val-DAB(Boc)-2-CTC Resin peptide resin is obtained; and after the peptide resin is cut and purified, tetradecyl aminobutyroylvalylaminobutyric urea trifluoroacetate, the purity of which is greater than 95 percent, is obtained. The synthesis method disclosed by the invention is simple and efficient, the cost is lower, and the purity and yield of the product are high.

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] Tetradecyl aminobutyryl valinyl amidobutyric acid urea trifluoroacetate is also known as hyaluronic acid peptide, its sequence is CH 3 (CH 2 ) 12 CH 2 NH-CO-DAB-Val-DAB-OH is a tripeptide modified by tetradecylcarbamoyl, which can act on the dermis to increase the synthesis of collagen fibers by promoting the synthesis of natural skin hyaluronic acid, thereby Improve skin sagging, widely used in various advanced beauty cosmetics. [0003] At present, there are few reports on the synthetic method of tetradecylaminobutyryl valyl amidobutyric acid urea trifluoroacetate, so the simple and convenient tetradecyl aminobutyryl valyl amido butyric acid urea trifluoroacetate is developed. The acetate synthesis method has practical significance. Contents of the invention [0004] Th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/09C07K1/06C07K1/04C07K1/02
CPCC07K5/0815
Inventor 张忠旗郭添王万科李乾韩广刘少军杨小琳赵金礼
Owner SHAANXI HUIKANG BIO TECH CO LTD