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Method for synthesizing tesamorelin through solid phases

A technology of temorelin and solid phase synthesis, which is applied in the field of preparation of solid phase peptide synthesis of temorelin, can solve the problems of expensive raw materials and long reaction time, and achieve the effects of low cost, convenient source and low production odor

Inactive Publication Date: 2012-10-03
GL BIOCHEM SHANGHAI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of high yield, low cost, the reaction raw material is simple and easy to obtain, and the solid-phase synthesis technique of temorelin that utilizes realizes industrialization mainly solves the reaction time that existing synthetic method exists is long, raw material expensive technical issues

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] The list of raw materials adopted in the embodiment and the foregoing process is as follows:

[0083] NO Raw material and reagent name source 1. Rink Amide AM Resin Jill Biochemical (Shanghai) Co., Ltd. 2 Rink Amide MBHA Resin Jill Biochemical (Shanghai) Co., Ltd. 3 Fmoc-Tyr(tbu)-OH Jill Biochemical (Shanghai) Co., Ltd. 4 Fmoc-Ala-OH Jill Biochemical (Shanghai) Co., Ltd. 5 Fmoc-Asp(otbu)-OH Jill Biochemical (Shanghai) Co., Ltd. 6 Fmoc-Ile-OH Jill Biochemical (Shanghai) Co., Ltd. 7 Fmoc-Phe-OH Jill Biochemical (Shanghai) Co., Ltd. 8 Fmoc-Thr(tbu)-OH Jill Biochemical (Shanghai) Co., Ltd. 9 Fmoc-Asn(Trt)-OH Jill Biochemical (Shanghai) Co., Ltd. 10 Fmoc-Ser(tbu)-OH Jill Biochemical (Shanghai) Co., Ltd. 11 Fmoc-Arg(pbf)-OH Jill Biochemical (Shanghai) Co., Ltd. 12 Fmoc-Lys(Boc)-OH Jill Biochemical (Shanghai) Co., Ltd. 13 Fmoc-Val-OH Jill Biochemical (Shanghai) Co....

Embodiment 2

[0177] Use Rink Amide AM resin as the starting material, weigh 100g of the resin (100-200 mesh, 0.27mmol / g, 27mmol), swell in DCM for 20 minutes, add Fmoc-Leu-OH, HBTU, HoBt, and dissolve with coupling reagent The mixture was reacted at 40°C for 2 hours, washed with NMP and anhydrous ether for 3-6 times respectively. The volume ratio of the coupling reagent is: NMM:NMP=1:12, and the weight ratio of the volume of the coupling reagent to the resin is 10ml / g. The component and volume ratio of the deprotection reagent is: PIP:NMP=1:4, and the weight ratio of the volume of the deprotection reagent to the resin is 10ml / g.

[0178] Add deprotection reagent, react at 20°C for 30 minutes, add Fmoc-amino acid dissolved in coupling reagent, HBTU / HoBt or DIC / HoBt mixture after washing fully, react at 40°C for 2 hours, and operate as in Example 1 for the rest until obtaining Temorelin crude peptide resin was subjected to cleavage and other reactions to obtain 131.7 g of crude product of T...

Embodiment 3

[0181] Use Rink Amide AM resin as the starting material, weigh 100g of the resin (100-200 mesh, 0.27mmol / g, 27mmol), swell in DCM for 10 minutes, add Fmoc-Leu-OH, Bop, HoBt, and dissolve it with a coupling reagent The mixture was reacted at 50°C for 30 minutes, washed with NMP and anhydrous ether for 3-6 times respectively. The volume ratio of the coupling reagent is: NMM:NMP=1:20, and the weight ratio of the volume of the coupling reagent to the resin is 15ml / g. The component and volume ratio of the deprotection reagent is: PIP:NMP=1:6, and the weight ratio of the volume of the deprotection reagent to the resin is 15ml / g.

[0182] Add deprotection reagent, react at 50°C for 10 minutes, add Fmoc-amino acid dissolved in coupling reagent, Bop / HoBt or PyBop / HoBt mixture after washing fully, react at 50°C for 30 minutes, and operate in the same manner as in Example 1 until obtaining The temorelin crude peptide resin was subjected to cleavage and other reactions to obtain 110.9 g ...

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Abstract

The invention provides a method for synthesizing tesamorelin through solid phases and mainly solves the technical problems of long reaction time and high raw material cost of the existing synthesis method. According to the method, RinkAmideAM resin or RinkAmide MBHA resin is used as initial raw materials, trans-hexenoic acid and amino acid with Fmoc protecting groups are sequentially connected, side-chain full-protection tesamorelin resin is synthesized and obtained, the side-chain group protection removal and the peptide cutting are synchronously carried out, the tesamorelin crude peptide is obtained, the separation purification is carried out through C18 or C4 columns, and products are obtained through freezing and drying. The method has the characteristics that the process is stable, resources of raw and auxiliary materials are convenient to obtain, the reaction operation is simple, the post treatment is easy, the yield is high, the cost is low, the production smell is low, and the like.

Description

technical field [0001] The invention relates to a preparation method of temorelin, in particular to a preparation method of solid-phase polypeptide synthesis of temorelin. Background technique [0002] Chinese name: Temorelin or Temorelin acetate. Trade name: Egrifta. English name: tesamorelin. Structural formula: trans-Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu- Gln-Asp-Ile-Met-Ser-Arg-Gln-Gln-Gly-Glu-Ser-Asn-Gln-Glu-Arg-Gly-Ala-Arg-Ala-Arg-Leu-NH 2 ;Molecular formula: C221H366N72067S1, molecular weight: 5135.9. [0003] AIDS is a public health problem that seriously threatens the health of people all over the world. In 1983, human beings discovered HIV for the first time. Currently, AIDS has changed from a fatal disease to a manageable chronic disease. The number of AIDS patients in our country is also increasing year by year. It is no secret that the side effects of AIDS drugs are lipodystrophy. Lipodystrophy is man...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/60C07K1/20C07K1/06C07K1/04
CPCY02P20/55
Inventor 徐红岩吴逸璘张宏伟
Owner GL BIOCHEM SHANGHAI
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