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Liraglutide synthesis method

A technology of liraglutide and synthetic methods, which is applied in the field of peptide drug synthesis and can solve problems such as difficult sequence synthesis

Active Publication Date: 2018-10-19
SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In order to solve the deficiencies of the prior art, the object of the present invention is to provide a synthetic method of liraglutide. This method obtains a fully protected peptide resin by introducing Depsipeptide Units, and then undergoes cleavage and ester bond to amide bond reaction to obtain the target product; the introduction of Depsipeptide Units can solve the difficult sequence synthesis problem of liraglutide; greatly improve the purity and yield of the crude peptide synthesized

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Embodiment Construction

[0059] The present invention will be specifically introduced below in conjunction with the accompanying drawings and specific embodiments.

[0060] There are two options for preparing liraglutide:

[0061] Such as figure 1 As shown, option one:

[0062] A synthetic method of liraglutide, comprising the steps of:

[0063] Step 1, prepare Fmoc-Gly-Wang resin;

[0064] Step 2, preparing fully protected peptide resin;

[0065] Step a, preparing protected amino acid fragments,

[0066] The chemical structural formula of the protected amino acid fragment is:

[0067] Where R includes: H, CH 3 (Ser,Thr); Thr in peptide sequence 5 、Thr 7 、Ser 8 、Ser 11 、Ser 12 ; That is, the chemical formula for protecting amino acid fragments includes: Boc-Thr 5 (Fmoc-Gly 4 )-OH, Boc-Thr 7 (Fmoc-Phe 6 )-OH, Boc-Ser8(Fmoc-Thr 7 (tBu))-OH, Boc-Ser 11 (Fmoc-Val 10 )-OH, Boc-Ser 12 (Fmoc-Ser 11 (tBu))-OH.

[0068] In step b, the Fmoc-Gly-Wang resin is added to the solid phase react...

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Abstract

The invention discloses a liraglutide synthesis method, which comprises the following steps: 1, preparing a Fmoc-Gly-Wang resin; 2, preparing a fully-protected peptide resin from the Fmoc-Gly-Wang resin, protected amino acid and Pal-Glu, the fully-protected peptide resin comprising Depsipeptide Units; 3, performing TFA pyrolysis on the peptide resin to obtain crude peptide; 4, dissolving the crudepeptide obtained in Step 3, regulating the PH and performing ester bond to amido bond reaction to obtain a liraglutide crude product. According to the method, the Depsipeptide Units are introduced toobtain the fully-protected peptide resin and then pyrolysis and ester bond to amido bond reaction are performed to obtain a target product; by introduction of the Depsipeptide Units, problems about synthesis of difficult sequences of the liraglutide can be solved, and the purity and the yield of the synthesized crude peptide can be greatly improved.

Description

technical field [0001] The invention relates to the field of polypeptide drug synthesis, in particular to a method for synthesizing liraglutide. Background technique [0002] Chinese name: Liraglutide [0003] English name: Liraglutide [0004] The peptide sequence is: [0005] H-His 1 -Ala 2 -Glu 3 -Gly 4 -Thr 5 -Phe 6 -Thr 7 -Ser 8 -Asp 9 -Val 10 -Ser 11 -Ser 12 -Tyr 13 -Leu 14 -Glu 15 -Gly 16 -Gln 17 -Ala 18 -Ala 19 -Lys 20 (Pal-γ-Glu)-Glu 21 -Phe 22 -Ile 23 -Ala24-Trp 25 -Leu 26 -Val 27 -Arg 28 -Gly 29 -Arg 30 -Gly 31 -OH [0006] Liraglutide is the first long-acting GLP-1 analogue developed by Novo Nordisk, Denmark. It is 97% homologous to human glucagon-like peptide-1 (GLP-1). Liraglutide has various effects such as lowering blood sugar, promoting regeneration of islet cells, and slightly prolonging gastric emptying, and has broad application prospects. [0007] Depsipeptide Units is a lipopeptide structural unit, which has been descri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/605C07K1/06C07K1/04
CPCC07K14/605Y02P20/55
Inventor 赵呈青谷海涛施国强
Owner SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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