首页> 外国专利> MILD AND EFFICIENT PREPARATION METHOD FOR Α-ACYLOXY ALKENYL AMIDE COMPOUND AND USE THEREOF IN SYNTHESIS OF AMIDE AND POLYPEPTIDE

MILD AND EFFICIENT PREPARATION METHOD FOR Α-ACYLOXY ALKENYL AMIDE COMPOUND AND USE THEREOF IN SYNTHESIS OF AMIDE AND POLYPEPTIDE

机译：α-乙酰环戊烯酰胺化合物的温和高效制备方法及其在酰胺和多肽合成中的应用

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摘要

Disclosed are a mild and efficient preparation method for an α-acyloxy alkenyl amide compound and a use thereof in the synthesis of an amide and a polypeptide. The α-acyloxy alkenyl amide compound is obtained by an addition reaction of an alkyne amide and a carboxylic acid in dichloromethane under conditions where the temperature is 0ºC to 50ºC; the produced α-acyloxy alkenyl amide compound can be reacted with an amide compound to produce an amide or a polypeptide; the two reactions can be carried out step by step, and can also be carried out in one pot; and when the two reactions are carried out in one pot, the produced α-acyloxy alkenyl amide compound does not need to be purified from the former reaction and the amide compound is directly added for reaction. In the reaction where the amide or the polypeptide is produced, the solvent can also be water, wherein same provides a novel method for fixed-site modification and marking of biological macromolecules including proteins, nucleic acid and the like in a water phase. According to the present invention, the reaction conditions are mild and no metal catalyst is required; when the carboxylic acid, which has chirality on an alpha site of carboxyl, forms an amide bond or a peptide bond, no racemization occurs; and the operation is simple and the application range is wide.

机译：公开了一种温和有效的α-酰氧基烯基酰胺化合物的制备方法及其在酰胺和多肽的合成中的用途。 α-酰氧基烯基酰胺化合物是通过在温度为0ºC至50ºC的条件下，炔烃酰胺与羧酸在二氯甲烷中的加成反应而制得的;所产生的α-酰氧基烯基酰胺化合物可以与酰胺化合物反应以产生酰胺或多肽。这两个反应可以逐步进行，也可以在一个锅中进行。当在一个锅中进行两个反应时，不需要从前一个反应中纯化得到的α-酰氧基烯基酰胺化合物，而是直接加入酰胺化合物进行反应。在产生酰胺或多肽的反应中，溶剂也可以是水，其中溶剂提供了用于在水相中对包括蛋白质，核酸等在内的生物大分子进行固定位点修饰和标记的新颖方法。根据本发明，反应条件温和，不需要金属催化剂。当在羧基的α位具有手性的羧酸形成酰胺键或肽键时，不发生外消旋化;操作简单，适用范围广。

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公开/公告号WO2018018863A1

专利类型
公开/公告日2018-02-01

原文格式PDF
申请/专利权人 JIANGXI NORMAL UNIVERSITY;
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申请/专利号WO2017CN71910
发明设计人 ZHAO JUNFENG;HU LONG;XU SILIN;ZHAO ZHENGUANG;
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申请日2017-01-20
分类号C07C303/40;C07C311/17;C07D307/68;C07D231/56;C07D333/68;C07D209/20;C07D263/22;C07C231/02;C07K5/078;C07K5/06;C07C233/05;
国家 WO
入库时间 2022-08-21 12:46:11

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