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Preparation method of synthesizing octriotide from solid phase polypeptide

A technology for solid-phase peptide synthesis and octreotide, which is applied in the production of peptides and bulk chemicals, and can solve problems such as low yield, environmental pollution, and high production costs

Active Publication Date: 2010-12-22
SHANGHAI SOHO YIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] At present, the preparation methods reported in the literature all have certain defects. Trifluoroacetic acid must be used for each round of decapping, so the peptide yield is low, resulting in high production costs; the three wastes are polluted, and hydrogen fluoride is used to cut peptides and trifluoroacetic acid. Purification, pollute the environment, low yield
Therefore, current methods limit the large-scale production and use of octreotide

Method used

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  • Preparation method of synthesizing octriotide from solid phase polypeptide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The list of raw materials adopted in the embodiment and the foregoing process is as follows:

[0073] 1. Synthetic peptide chain

[0074] (1) Preparation of Fmoc-Thr(tBu)-resin:

[0075] Take 50 grams of 2-chloro-trityl resin (100-200 mesh, 1.0mmol / g, 50mmol), soak in DMF for 30 minutes to fully swell the resin, add 44ml DIPEA, 39.7g Fmoc-Thr(tBu)- ol, reacted for 3 hours, then added 50ml of methanol to continue the reaction for 3 hours. Blow dry with nitrogen, and wash the resin three times with DMF. Obtain Fmoc-Thr(tBu)-resin;

[0076] (2) Preparation of Fmoc-Cys(Trt)-Thr-resin:

[0077] Add 800 ml of 20% hexahydropyridine in DMF and react at 25° C. for 30 minutes. Hexahydropyridine was blown and filtered with nitrogen, washed with DMF, anhydrous methanol, and DMF three times respectively, and dried with nitrogen.

[0078] Add Fmoc-Cys(Trt)-OH (MW: 585.7, 200mmol) 117.1g, TBTU (MW: 321, 200mmol) 64.2g, HOBT (MW: 153, 200mmol) 30.6g, NMM 44.4ml (MW = 101.2), ...

Embodiment 2～3

[0106] Adopt the same method and processing condition as embodiment 1, wherein:

[0107] Use 4-methyltrityl resin or 4-methoxytrityl resin as the starting material respectively, connect Fmoc-Thr-ol with the same method as before, then add decapping reagent, react at 25°C for 0.5 hours, Add the mixture of Fmoc-amino acid, TBTU / HBTU and HOBT dissolved in the peptide reagent, react at 25°C for 2 hours, and then undergo reactions such as peptide cutting and oxidation to obtain 16.3g and 14.9g of white loose block products, the yields are respectively 32.0% and 29.2% (in mmol of Fmoc-Thr-resin).

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Abstract

The invention discloses an aoqu-peptide preparing method of solid-phase polypeptide, which comprises the following steps: adopting 2-chloride-trityl resin, 4-methyl trityl resin or 4-methoxyl trityl resin as raw material; connecting amino acid with protective group according to solid-phase synthetic method; obtaining protected octapeptide resin; removing Fmoc-protective group sequently; strippingside-chain protective group; cutting peptide to obtain reduced aoqu-peptide; oxidizing through air under pH 7-11 condition; separating and purifying rought product through C18 (C8) column to produce exquisite.

Description

technical field [0001] The invention relates to a preparation method of octreotide, in particular to a preparation method of solid-phase polypeptide synthesis of octreotide. Background technique [0002] Octreotide, Chinese name: Octreotide acetate; English name: Octreotide Acetate [0003] Structural formula: [0004] [0005] Molecular formula: C 49 h 66 N 10 o 10 S 2 ·XC 2 h 4 o 2 [0006] Octreotide is a synthetic somatostatin 8 peptide, which is one of the most effective hormone drugs in clinical application in the 1990s. It has the same pharmacological effect as natural somatostatin, but its half-life is 30 times longer, so it has application value. Octreotide can inhibit the secretion of a variety of gastrointestinal hormones and other endocrine functions, and has been widely used in the clinical treatment of various types of pancreatitis, pancreatic fistula, intestinal fistula, liver cirrhosis, esophagus-gastric variceal bleeding, and pep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/64C07K7/06
CPCY02P20/55
Inventor 周逸明
Owner SHANGHAI SOHO YIMING PHARMA
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