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Liquid-phase synthesis method of palmitoyl tripeptide-1

A technology of palmitoyl tripeptide and liquid phase synthesis, which is applied in the field of drug synthesis, can solve the problems of high cost, non-environmental protection, and complicated process, and achieve the effects of low cost, environmental protection, and simple preparation process

Inactive Publication Date: 2018-06-29
GUANGZHOU TROJAN PHARMATEC LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing liquid-phase synthesis method is complex in process and uses a large amount of organic solvents, which is costly and not environmentally friendly.

Method used

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  • Liquid-phase synthesis method of palmitoyl tripeptide-1

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Effect test

Embodiment 1

[0027] A kind of embodiment of palmitoyl tripeptide-1 liquid phase synthesis method of the present invention, comprises the following steps:

[0028] (1) Synthesis of Pal-Gly-OH

[0029] According to the molar ratio of glycine, sodium hydroxide and palmitoyl chloride as 1.0:2.2:1.1, put 15.1g of glycine in a 500mL reaction flask, add 75.5mL of tert-butanol, and add 22.5mL of 30% mass fraction under stirring conditions sodium hydroxide solution, stirred until clear; cooled to 0-5 ° C, and at the same time 67.2 mL of palmitoyl chloride and 22.5 mL of sodium hydroxide solution with a mass fraction of 30% were added dropwise, the temperature was controlled below 5 ° C, and the pH of the reaction system was controlled. At 8.5, after the dropwise addition, warm up to room temperature and stir for 2 hours, cool down to below 10°C, add hydrochloric acid dropwise to adjust the pH to 2-3, filter, wash with water, and dry to obtain the crude product, which is refluxed with 300mL dichloro...

Embodiment 2

[0042] An embodiment of the palmitoyl tripeptide-1 liquid phase synthesis method of the present invention, except that the molar weight of palmitoyl chloride used in the step (1) of the synthesis of Pal-Gly-OH is 1.3 of the molar weight of palmitoyl chloride in embodiment 1 Except that, other steps were the same as in Example 1 to obtain 53.2 g of palmitoyl tripeptide-1, with a yield of 92.3% and a purity greater than 98%.

Embodiment 3

[0044] An embodiment of the palmitoyl tripeptide-1 liquid phase synthesis method of the present invention, except that the molar weight of palmitoyl chloride used in the step (1) of the synthesis of Pal-Gly-OH is 9% of the molar weight of palmitoyl chloride in embodiment 1 / 10 times, other steps are the same as in Example 1, the quality of palmitoyl tripeptide-1 obtained is 51.8g, the yield is 90%, and the purity is greater than 98%.

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Abstract

The invention discloses a liquid-phase synthesis method of palmitoyl tripeptide-1. The liquid-phase synthesis method comprises the following steps of synthesizing the palmitoyl tripeptide-1 by sections, and respectively synthesizing a dipeptide segment H-His-Lys(Z)-OBzl and the other segment Pal-Gly-OH in a sequence of the palmitoyl tripeptide-1; synthesizing the two segments into a palmitoyl tripeptide segment by an active ester method; then, performing hydrogenation reaction, so as to obtain a final product of palmitoyl tripeptide-1. The liquid-phase synthesis method has the advantages thatthe defects of forcible protection on amino acid in each step of solid-phase reaction, multiple solvent types, obvious excessive reagent and difficulty in recycling of solvent are overcome; the synthesizing method is simple, the product cost is low, the greener effect to environment is realized, and the like; the large-scale production effect is realized, and palmitoyl tripeptide-1 can be producedin an industrialization way.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a liquid phase synthesis method of palmitoyl tripeptide-1. Background technique [0002] Palmitoyl tripeptide-1 can greatly promote the production of collagen in the skin, make the facial skin plump and give elasticity, increase the water content and moisture retention of the skin, make the skin soft and smooth to the touch, and brighten the complexion from the inside out without dullness. [0003] The synthesis methods of palmitoyl tripeptide-1 include traditional solid-phase peptide synthesis and liquid-phase peptide synthesis methods. Due to its short sequence, solid-phase synthesis of amino acids requires a large amount of amino acids, high cost, and it is difficult to achieve large-scale preparation; liquid-phase synthesis method The dosage of amino acid is small, the yield is high, and it can be prepared in large quantities. However, the existing liquid-...

Claims

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Application Information

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IPC IPC(8): C07K5/083C07K1/36C07K1/02C07K1/06C07K1/30
CPCC07K5/0806C07K19/00
Inventor 郑庆泉
Owner GUANGZHOU TROJAN PHARMATEC LTD
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