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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 polypeptide preparation, can solve the problems of being unsuitable for large-scale production, prolonging the process cycle, and prone to explosion, etc., and achieves environment-friendly production conditions, simple process route, and mild reaction Effect

Inactive Publication Date: 2021-02-26
ZHEJIANG PEPTITES BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The publication number is CN108218956A, and the patent name is a liquid-phase synthesis method of palmitoyl tripeptide-1. In the route recorded in the invention patent, Pal-Gly-ONb needs to be synthesized, and the residual Pal-OH of the raw material is difficult to quantify when synthesizing Pal-Gly Detection, HPLC can not truly reflect the actual residual status of raw materials, because the synthesis of route fragments needs to calculate the feeding amount according to the synthesis of another fragment, so the problem that the intermediate Pal-Gly-ONb has high activity and is not easy to store will make it difficult to carry out large-scale production. The removal of Boc-His(Trt)-Lys(Z)-OBzl requires a large amount of TFA, which is highly corrosive to human skin and equipment, and is easy to pollute the environment. The last step of hydrogenation and hydrogenation is also very dangerous and prone to explosion. Risky, not suitable for large-scale production. Another disadvantage of this route is that multiple reactions must be carried out at 0 degrees Celsius and in a reflux state. The requirements for equipment are high, and the energy utilization efficiency is not high. The cooling and heating time will lead to a longer process cycle.

Method used

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  • Liquid-phase synthesis method of palmitoyl tripeptide-1
  • Liquid-phase synthesis method of palmitoyl tripeptide-1

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Synthesis of Boc-Lys(Z)-OBzl

[0038] Start stirring and pump in 20L of acetone, add Boc-Lys(Z)-OH10kg, add potassium carbonate 3.81kg, add Bzl-Br4.72kg and stir for reaction. The reaction time is about 3h. If there is no raw material point on the TLC plate, it is judged that the reaction is over. Use vacuum pumping Add 20L of water, add 20L of ethyl acetate to extract twice, combine the organic phase into 20L of water, wash twice, wash once with 20L of saturated saline, add anhydrous sodium sulfate to the organic phase, dry, filter, rinse with ethyl acetate, and spin dry used directly in the next reaction.

[0039] (2) Synthesis of H-Lys(Z)-OBzl

[0040] Connect to the first step reactor and continue to operate, turn on the stirring, pump in DCM30L, weigh MS-OH3.03kg and add it, stir evenly and release it into the bucket, let it stand for reaction, the reaction time is about 2h, HPLC monitoring determines that the reaction is over, directly drop step.

[0041] (...

Embodiment 2

[0055] (1) Synthesis of Boc-Lys(Z)-OBzl

[0056] Start stirring and pump in DMF20L, add Boc-Lys(Z)-OH10kg, add cesium carbonate 11.2kg, add Bzl-Br4.58kg and stir for reaction. The reaction time is about 4h. If there is no raw material point on the TLC plate, it is judged that the reaction is over. Use vacuum to pump water 20L, add 20L of ethyl acetate to extract twice, merge the organic phase into 20L of water and wash twice, wash once with 20L of saturated saline, add anhydrous sodium sulfate to the organic phase to dry, filter, rinse with ethyl acetate, spin dry and directly for the next reaction;

[0057] (2) Synthesis of H-Lys(Z)-OBzl

[0058] Connect to the first step reaction kettle and continue to operate, start stirring, pump in THF35L, weigh MS-OH3.05kg and add it, stir evenly and release it into the barrel, let it stand at room temperature for reaction, the reaction time is about 3h, HPLC monitoring determines the end of the reaction, Directly vote for the next ste...

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Abstract

The invention discloses a liquid-phase synthesis method of palmitoyl tripeptide-1. The method comprises the following steps: synthesizing polypeptide Pal-Gly-His-Lys-OH by taking raw materials Boc-Lys(Z)-OH, MS-OH, Boc-His-OH and Boc-Gly-OH as raw materials and taking DIC / HOBt, DIC / HOAt, EDC / HOBt, HATU, HBTU and the like as reagents; then cutting off a protecting group Boc under an acidic condition; and purifying to obtain a product. The product is obtained by the liquid-phase synthesis method disclosed by the invention; the product is obtained by utilizing simple and conventional reactions in a process; each step of reaction is easy to detect and control; a key intermediate is easy to separate and store; and after hydrogenation, a high-purity product can be obtained without purification.The liquid-phase synthesis method is suitable for industrial large-scale production.

Description

technical field [0001] The present invention relates to the preparation method of polypeptide. More specifically, the present invention relates to the preparation method of Pal-Gly-His-Lys-OH. Background technique [0002] Pal-Gly-His-Lys-OH 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 of the skin and lock in moisture, and make the skin feel soft and greasy from the inside out Extra brightening complexion no longer dull. [0003] The publication number is CN108218956A, and the patent name is a liquid-phase synthesis method of palmitoyl tripeptide-1. In the route recorded in the invention patent, Pal-Gly-ONb needs to be synthesized, and the residual Pal-OH of the raw material is difficult to quantify when synthesizing Pal-Gly Detection, HPLC can not truly reflect the actual residual status of raw materials, because the synthesis of route fragments needs to calcul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/083C07K1/02C07K1/06
CPCC07K5/0806Y02P20/55
Inventor 黄毅邢海英王志国虞新友
Owner ZHEJIANG PEPTITES BIOTECH CO LTD
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