Liquid-phase synthesis method of snake venom-like tripeptide

A liquid-phase synthesis, snake venom technology, applied in the preparation methods of peptides, chemical instruments and methods, peptides, etc., can solve the problems of product quality impact, reaction difficulties, process control difficulties, etc.

Inactive Publication Date: 2021-03-02
ZHEJIANG PEPTITES BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, in the connection reaction between Boc-β-Ala-Pro-Dab(Boc)-OH and benzylamine, because the main chain amino acid of Dab(Boc) is not an oxycarbonyl protecting group, it is very easy to produce Dab in the condensation reaction. The racemization has a great influence on the product quality
[0005] Publication No. CN107857797A, the technical route mentioned in the invention patent whose patent name is a liquid-phase fragment synthesis method of snake venom tripeptide, firstly Fmoc-Pro-OH is prepared into Fmoc-Pro-OSu and H-Dab(Boc )-OH reaction forms the reaction process of Fmoc-Pro-Dab(Boc)-OH, the reaction will be more difficult due to the larger steric hindrance of Pro amino acid, and the yield will be lower; in addition, in Fmoc-Pro-Dab( In the connection reaction between Boc)-OH and benzylamine, because the Dab(Boc) main cha

Method used

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  • Liquid-phase synthesis method of snake venom-like tripeptide
  • Liquid-phase synthesis method of snake venom-like tripeptide
  • Liquid-phase synthesis method of snake venom-like tripeptide

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Embodiment Construction

[0037] The embodiment of the liquid phase synthesis method of a kind of snake venom tripeptide of the present invention is described further:

[0038] (1) Synthesis of Fmoc-Dab(Boc)-NHBzl

[0039] Add 18L DMF to the 100L reaction tank, add Fmoc-Dab(Boc)-OH (200.0g, 454mmol) and HoBT (79.9g, 590mmol), BnNH2 (48.6g, 454mmol), NMM (59.7g, 590mmol), and then Add 2L of DMF to wash, stir to dissolve, slowly add EDCI (1132.2g, 5906mmol), and stir at room temperature overnight.

[0040] TLC detected that the reaction of the raw materials was complete, and the reaction solution was added to a large amount of water to precipitate a viscous solid, then the supernatant was discarded, and the solid was washed with water. The solid was dissolved in DCM, and the layers were separated after dissolution, and the aqueous phase was removed. The DCM layer was dried over magnesium sulfate and filtered to obtain a DCM solution. The DCM was removed by rotary evaporation to obtain 200 g of a white...

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Abstract

The invention discloses a liquid-phase synthesis method of snake venom-like tripeptide. The method comprises the following steps: using raw materials Fmoc-Da (Boc)-OH, benzylamine, Boc-beta-Ala-OH andH-Pro-OMe. HCl/H-Pro-OBzl. HCl as raw materials and DIC/HOBt, DIC/HOAt, EDC/HOBT, HATU, HBTU and the like as reagents, synthesizing polypeptide H-beta-Ala-Pro-Dab(Boc)-NHBzl, then cutting off a protective group Boc under an acidic condition and purifying to obtain the product. The product H-beta-Ala-Pro-Dab(Boc)-NHBzl is directly obtained by using a solid-phase synthesis method, the stability problem of CTC resin is solved in the product, the racemization problem of Dab is avoided by adopting a method of connecting Fmoc-Db (Boc)-OH and benzylamine, and the synthesis method is short in processroute, very short in production period, suitable for large-scale production, good in method stability and suitable for 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 H-β-Ala-Pro-Dab-NHBzl. Background technique [0002] H-β-Ala-Pro-Dab-NHBzl is a small molecular peptide that mimics the activity of snake venom Waglerin I. Clinical trials have shown that this peptide can reduce wrinkles by inhibiting muscle contraction, and has excellent smoothing and rapid wrinkle removal properties , H-β-Ala-Pro-Dab-NH-Bzl acts on the postsynaptic membrane and is a reversible antagonist of the muscle nicotinic acetylcholine receptor (mmAChR), looking for a suitable synthetic method for the small molecular polypeptide Industrialization is of great significance. [0003] Commonly used chemical synthesis methods for peptide synthesis include liquid-phase synthesis and solid-phase synthesis. For small molecule peptides, generally less than 10 amino acids, the common method is to use liqu...

Claims

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Application Information

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IPC IPC(8): C07K5/083C07K1/02C07K1/06
CPCC07K5/0806Y02P20/55
Inventor 黄毅邢海英刘志国虞新友
Owner ZHEJIANG PEPTITES BIOTECH CO LTD
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