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Method for preparing somatostatin through solid-phase peptide synthesis

A technology for solid-phase peptide synthesis and somatostatin, which is applied to peptide preparation methods, chemical instruments and methods, peptides, etc., can solve the troublesome operation of pentapeptides, limit the large-scale production and use of somatostatin, and troublesome operation of dipeptides And other issues

Inactive Publication Date: 2013-03-06
SHANGHAI SOHO YIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The significant defects in this patent are: (1) the condensation reaction time with DCC is long, the production cycle is too long, (2) the preparation of dipeptide is troublesome, (3) there are many wastes in DMSO oxidation, (4) medium pressure chromatographic column Chromatographic purification is slower and less precise
The disadvantages of this method are: (1) the operation of preparing pentapeptide, tripeptide and hexapeptide is cumbersome, and the reaction cycle is also very long; (2) no separation and purification
The disadvantages of this method are: (1) the operation of preparing 4 tetrapeptides is cumbersome and the reaction cycle is very long
(2) The air oxidation reaction takes 2-3 days, which is not suitable for industrial production, (3) the specificity of 0.1% TFA for separation and purification is poor
[0010] Therefore, current methods limit the large-scale production and use of somatostatin

Method used

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  • Method for preparing somatostatin through solid-phase peptide synthesis
  • Method for preparing somatostatin through solid-phase peptide synthesis
  • Method for preparing somatostatin through solid-phase peptide synthesis

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Embodiment 1

[0084] The list of raw materials adopted in the embodiment and the foregoing process is as follows:

[0085]

[0086]

[0087] Example 1

[0088] (1) Production of Fmoc-Cys(Trt)-resin

[0089] Weigh 2.22kg of 2-chlorotriphenyl alcohol resin (100-150 mesh, 0.7mmol / g), put it into a 50L polypeptide synthesizer, add 14LDCM, stir and swell at room temperature for 1 hour. Under stirring, 3.6 kg of thionyl chloride (d=1.638) was slowly added dropwise through a constant pressure funnel within 30 minutes, and then stirred and reacted at room temperature for 3 hours.

[0090] Drain, wash with 72LDCM 6 times, each time with 12LDCM, stir for 15 minutes and then drain.

[0091] Add 7L of DMF, then add 1.76kg of Fmoc-Cys(Trt)-OH dissolved in 7L of DMF, and 1.187kg of DIPEA, and react at 35±3°C for 1.5 hours. Add 2.5 L of methanol and react at 34.5±2.5°C for 30 minutes. Drained, the resin was washed once with methanol, washed five times with DMF, and dried.

[0092] (2) Productio...

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Abstract

The invention provides a method for preparing somatostatin through solid-phase peptide synthesis. The method comprises the steps that: 2-chloro triphenyl alcohol resin is adopted as an initial raw material; amino acids with protective groups are sequentially connected with a solid-phase synthesis method; Fmoc- protective groups are sequentially removed; a peptide grafting reaction is carried out with TBTU and HOBT as condensing agents; after protected reduction-type 14-peptide resin is obtained, side-chain protective group removing and peptide cutting are carried out simultaneously, such that reduction-type somatostatin is obtained; the reduction-type somatostatin is oxidized by using hydrogen peroxide under a pH of 7-9, such that a somatostatin crude product is obtained; separation purification is carried out by using C18 high-performance liquid column; lyophilization is carried out, such that somatostatin refined product is obtained. The method provided by the invention has the advantages of capability of large-scale production, stable process, low production cost, reduced three-waste, reduced by-product, stable quality, low production cost, and high market competitiveness.

Description

technical field [0001] The invention relates to a production method of somatostatin, in particular to a new production process of solid-phase polypeptide synthesis of somatostatin. Background technique [0002] Chinese name: somatostatin. Other names: somatostatin-releasing inhibitory hormone, trade name: stanine. English name: Somatostatin, Stilamin. [0003] Structural formula: [0004] [0005] Molecular formula and molecular weight: C 76 h 104 N 18 o 19 S 2 , 1637.9. [0006] Clinical use: severe acute esophageal variceal rupture and bleeding, severe acute gastric and duodenal ulcer bleeding, acute erosive gastritis or hemorrhagic gastritis, adjuvant treatment of pancreas, gallbladder and intestines, adjuvant treatment of diabetic ketoacidosis. [0007] Patent application number 02155189.8 "New Method for Total Synthesis of Somatostatin" discloses a solid-phase peptide synthesis method. In this method, DCC is used as a condensation agent to synthesize 12 pept...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/08C07K1/06C07K1/04
CPCY02P20/55
Inventor 周逸明崔颀蔡华成
Owner SHANGHAI SOHO YIMING PHARMA
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