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Sincalide solid-liquid-phase synthesis method

A solid-phase synthesis method and synthesis method technology, which is applied in the field of solid-liquid phase synthesis of sincalide, can solve the problems of tedious, expensive raw materials and post-processing, and achieve simple operation, which is conducive to later industrial scale-up and high yield. Effect

Pending Publication Date: 2019-10-11
GL BIOCHEM SHANGHAI
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  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a high yield, low cost, mild reaction conditions, less environmental pollution, and a synthetic method for sincalide that is conducive to industrialization, and mainly solves the problems of expensive raw materials and cumbersome post-treatment in the prior art technical issues

Method used

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Embodiment

[0038] (1) Preparation of Fmoc-Asp-Phe-CONH 2

[0039] Weigh Fmoc-Asp (Otbu)-OSU 10.2g (MW: 508.5, 20mmol), NH 2 -Phe-CONH 2 3.61g (MW: 164.2, 22mmol) was added with 200ml tetrahydrofuran and 10ml DIEA, stirred for 2 hours, then extracted, washed, and evaporated to remove the solvent to obtain 12.1g of oil, and then added 100ml with a ratio of 95%TFA / 5%H 2 O(V / V) to remove the protecting group, stir the reaction for 1-2 hours, add ether to crystallize, remove the filtrate by suction filtration, and obtain a white solid filter cake which is the dipeptide fragment Fmoc-Asp-Phe-CONH 2 , 10.5 g of dipeptide fragments were obtained after drying.

[0040] (2) Preparation of Fmoc-Asp (β-2Cl-Trt Cl resin)-Phe-CONH 2

[0041] Weigh 20 g of dichlorotriphenyl chloride resin, add Fmoc-Asp-Phe-CONH 2 10.5g (MW: 501.5, 20mmol), add 300ml dichloromethane, 30mlDIEA, stir for 2 hours, add 200ml methanol, shake for 30 minutes, remove the filtrate by filtration, wash the resin 3 times wi...

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Abstract

The invention relates to a sincalide solid-liquid-phase combined synthesis method. The technical problems are mainly solved that raw materials are high in price and after-treatment is complicated in the prior art. According to the technical scheme, the sincalide solid-liquid-phase synthesis method includes the following steps of firstly, synthesizing an Fmoc-Asp-Phe-CONH2 dipeptide segment througha liquid phase method; secondly, loading the dipeptide segment on 2-chlorotrityl chloride resin to obtain Fmoc-Asp(beta-2Cl-Trt Cl resin)-Phe-NH2; thirdly, sequentially connecting residual protectionamino acids through a solid-phase synthesis method to obtain a sincalide resin peptide (Asp-Tyr(SO3H)-Met-Gly-Trp-Met-Asp(beta-2Cl-Trt Cl resin)-Phe-CONH2); fourthly, conducting cutting to obtain a crude sincalide product (Asp-Tyr(SO3H)-Met-Gly-Trp-Met-Asp-Phe-CONH2), and conducting efficient liquid-phase spectrum separation and purification and freeze-drying and refining on the crude product toobtain sincalide.

Description

technical field [0001] The invention relates to the technical field of polypeptide compound synthesis, in particular to a solid-liquid phase synthesis method of sincalide. Background technique [0002] Cholecystokinin (CCK) is a brain-gut peptide with multiple molecular forms and dual distribution, consisting of 33 amino acids, with hormone and neurotransmitter functions. Sincalide is an octapeptide molecule, which is a fragment of cholecystokinin and has all the biological activities of cholecystokinin. , a gallbladder diagnostic reagent, clinically used in the treatment of chronic pancreatitis, found that the pancreatic secretion function was significantly improved, and the symptoms were significantly relieved. The CAS number is: 25126-32-3, the molecular formula is C49H62N10O16S3, and the molecular weight is 1143.27. [0003] At present, the preparation methods of sincalide mainly include enzymatic method and chemical method. Among them, enzymatic synthesis involves ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/595C07K1/06C07K1/04
CPCC07K14/595Y02P20/55
Inventor 徐红岩竺剑峰
Owner GL BIOCHEM SHANGHAI
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