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Preparation method of octreotide

A technology of octreotide and crude peptide, which is applied in the field of solid-phase synthesis of octreotide, can solve the problems of carcinogenic by-products and low yield of octreotide, and achieve the effect of increasing product yield and shortening reaction time

Inactive Publication Date: 2010-10-20
苏州中科天马肽工程中心有限公司
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Problems solved by technology

However, when preparing octreotide from linear crude peptides, this method also uses the same air oxidation method as ZL200410010833.2, so that the yield of the final product octreotide is low; in addition, this method uses BOP as a condensation agent in the synthesis of octapeptides. Condensing agents produce carcinogenic by-products during use

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  • Preparation method of octreotide

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Embodiment Construction

[0028] The abbreviations used in the present invention have the following meanings:

[0029] Boc: tert-butoxycarbonyl; tBu: tert-butyl; BOP: benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate; Bzl: benzyl; 2-CTC: 2 -Chlorotrityl; DCM: dichloromethane; DIC: N,N-diisopropylcarbodiimide; DIPEA: N,N-diisopropylethylamine; DMF: N,N-dimethyl Formamide; EDT: 1,2-ethanedithiol; Fmoc: 9-fluorenylmethoxycarbonyl; HOBt: 1-hydroxybenzotriazole; TFA: trifluoroacetic acid; Trt: trityl; Z: benzyl Oxycarbonyl;

[0030] Fmoc-AA-OH: amino acid protected by N-fluorenylmethoxycarbonyl;

[0031] Fmoc-Cys(Trt)-OH: N-fluorenylmethoxycarbonyl-S-tritylcysteine;

[0032] Fmoc-Lys(Boc)-OH: N-α-fluorenylmethoxycarbonyl-N-ε-tert-butoxycarbonyllysine;

[0033] Fmoc-Phe-OH: N-fluorenylmethoxycarbonyl-phenylalanine;

[0034] Fmoc-D-Phe-OH: N-fluorenylmethoxycarbonyl-D-phenylalanine;

[0035] Fmoc-Thr(tBu)-OL: N-fluorenylmethoxycarbonyl-O-tert-butylthreoninol;

[0036] Fmoc-Thr(tBu)...

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Abstract

The invention relates to a preparation method of octreotide, which comprises the steps of preparing crude linear peptide by an Fmoc / tBu solid-phase peptide synthesis method and preparing octreotide from the crude linear peptide through oxidizing reaction, wherein the oxidizing reaction is carried out under the pH of 7.0-7.5 and in the presence of hydrogen peroxide, and the charging molar ratio of the hydrogen peroxide and the crude linear peptide is 7-9 / 1. The invention adopts the hydrogen peroxide to oxidize the crude linear peptide so as to obtain the octreotide, the oxidizing reaction can be finished only within 1-3h, compared with the traditional air oxidizing method, the reaction time is greatly shortened, the octreotide product yield is tremendously improved, and the method is suitable for mass production of the octreotide and salts thereof.

Description

technical field [0001] The invention relates to a preparation method of octreotide, in particular to a method for solid phase synthesis of octreotide. Background technique [0002] Octreotide, whose chemical name is D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophanyl-L-lysyl-L-threonyl-L-cysteine Acyl-L-threoninol ring 2→7) disulfide, its structural formula is as shown in formula (I). [0003] [0004] The synthetic methods of octreotide include liquid-phase fragment condensation method and solid-phase synthesis method, among which the solid-phase synthesis method is the main method. In the prior art, solid-phase synthesis generally includes the following steps: [0005] (1), connecting N-fluorenylmethoxycarbonyl-O-tert-butylthreoninol to the resin as a carrier to obtain N-fluorenylmethoxycarbonyl-O-tert-butylthreoninol resin; [0006] (2), according to the method of Fmoc / tBu solid-phase peptide synthesis, according to the sequence of octreotide, the protected ami...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/06C07K1/04
Inventor 王良友陆冬冬陈逸民王宝利
Owner 苏州中科天马肽工程中心有限公司
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