Synthesis method of snake venom-like tripeptide

A synthetic method and snake venom technology, applied in the field of synthesis of snake venom-like tripeptides, can solve the problems of difficult purification, low total yield, low purification yield, etc., achieve short synthesis process route, overcome stability problems, and purify The effect of high yield

Active Publication Date: 2022-01-07
浙江湃肽生物股份有限公司深圳分公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, most of the conventional methods for synthesizing snake venom-like tripeptides are liquid-phase synthesis and solid-phase synthesis, but the method of liquid-phase synthesis has many steps and is relatively cumbersome. , the total yield is not high, and the subsequent purification yield is low; using solid-phase synthesis, the purification is difficult and the yield is extremely low, and the limitations of each method are unavoidable when using solid-phase synthesis or liquid-phase synthesis

Method used

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  • Synthesis method of snake venom-like tripeptide
  • Synthesis method of snake venom-like tripeptide
  • Synthesis method of snake venom-like tripeptide

Examples

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Embodiment 1

[0063] This embodiment provides a synthetic method for a snake-like venom tripeptide, the synthetic route is as follows figure 1 As shown, the method includes:

[0064] Preparation of S1, H-Dab(Boc)-NHBzl:

[0065] In 600mL tetrahydrofuran, add 44gFmoc-Dab(Boc)-OH, 11.8g benzylamine, 14.2gNMM, stir at room temperature for 5min, add 235gEDCI, stir for 24h, add water to the product to precipitate a solid, wash with water, dissolve with dichloromethane, Separate the layers, dry the organic layer, filter, remove dichloromethane by rotary evaporation, add the obtained compound to 400 mL of tetrahydrofuran solution containing 15 vol% piperidine, stir at room temperature for 30 min, concentrate by rotary evaporation, add diethyl ether to precipitate, filter, and use Washed twice with ether and dried to obtain 27.6g of H-Dab(Boc)-NHBzl;

[0066] Preparation of S2, Boc-β-Ala-Pro-OH:

[0067] In 500mL tetrahydrofuran, add 18.9g Boc-β-Ala-OH, 16.6gH-Pro-OMe HCl, 1.65gHOBT, 10gNMM, sti...

Embodiment 2

[0082] This example provides another synthesis method of snake venom-like tripeptide, which differs from Example 1 only in that during the preparation of the modified PGMA-TCA chromatographic packing, the addition amount of anophylline is 6 g.

[0083] This example also provides an anti-wrinkle cosmetic, which differs from Example 1 only in that the snake venom-like tripeptide obtained in Example 1 is used instead of the snake-like venom tripeptide obtained in Example 1.

Embodiment 3

[0085] This example provides another synthesis method of snake venom-like tripeptide, which differs from Example 1 only in that during the preparation of the modified PGMA-TCA chromatographic packing, the addition amount of anophylline is 10 g.

[0086] This example also provides an anti-wrinkle cosmetic, which differs from Example 1 only in that the snake venom-like tripeptide obtained in Example 1 is used instead of the snake-like venom tripeptide obtained in Example 1.

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Abstract

The invention provides a synthetic method of snake venom-like tripeptide, and belongs to the technical field of polypeptide preparation methods, and the synthetic method specifically comprises the following steps: synthesizing crude snake venom-like tripeptide by taking Fmoc-Dab(Boc)-OH, benzylamine, Boc-[beta]-Ala-OH and H-Pro-OMe.HCl as raw materials; and purifying the snake venom-like tripeptide crude product by using a high performance liquid chromatography and anion exchange chromatography combined method to obtain the high-purity snake venom-like tripeptide, wherein the synthesis process route is short, the separation and purification effects are high, and the obtained high-purity snake venom-like tripeptide is high in purity and yield.

Description

technical field [0001] The invention belongs to the technical field of polypeptide preparation methods, and in particular relates to a method for synthesizing snake venom-like tripeptides. Background technique [0002] Snake venom-like tripeptide (H-β-Ala-Pro-DAB-NH-Bzl) is a small molecular polypeptide that mimics the activity of snake venom. Studies have found that snake venom-like tripeptide can achieve smoothness by relaxing facial muscles and reducing muscle contraction. and anti-wrinkle purposes. At present, Europe, America, South Korea, Thailand and other countries have developed cosmetics containing snake venom tripeptides, and snake venom tripeptides are becoming more and more popular as a new cosmetic ingredient in cosmetics. [0003] At present, most of the conventional methods for synthesizing snake venom-like tripeptides are liquid-phase synthesis and solid-phase synthesis, but the method of liquid-phase synthesis has many steps and is relatively cumbersome. ,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/083C07K1/04C07K1/06C07K1/18C07K1/16C07K1/14A61K8/64A61Q19/08
CPCC07K5/0806A61K8/64A61Q19/08
Inventor 王辉平刘慧敏傅小明应佳伟
Owner 浙江湃肽生物股份有限公司深圳分公司
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