N-酰基取代的7-氨基-4-氯异香豆素：一种通过酰亚胺机制的肽降解模型。

N-acyl substituted 7-amino-4-chloroisocoumarin: a peptide degradation model via an imide mechanism.

作者信息

Garino Cédrik, Bihel Frédéric, Souard Florence, Quéléver Gilles, Kraus Jean-Louis

机构信息

INSERM U-382, Institut de Biologie du Développement de Marseille, CNRS-INSERM-Université de la Méditerranée, Faculté des Sciences de Luminy, case 907, 13288 Marseille Cedex 09, France.

出版信息

Bioorg Med Chem Lett. 2004 Apr 5;14(7):1771-4. doi: 10.1016/j.bmcl.2004.01.030.

DOI:10.1016/j.bmcl.2004.01.030

PMID:15026068

Abstract

During the coupling reaction between 3-alkoxy-7-amino-4-chloroisocoumarin and N-acyl alanine dipeptide, an unexpected deamidation reaction was observed. The proposed mechanism for this reaction involved the formation of an imide intermediate which after cleavage led to the release of amino acid moiety. The described deamidation reaction represents the first chemical model involving a non-peptidic moiety, which mimics biological and chemical deamidation processes occurring in proteins or peptides incorporating an asparagine or a glutamine residue.

摘要

在3-烷氧基-7-氨基-4-氯异香豆素与N-酰基丙氨酸二肽的偶联反应过程中，观察到了意外的脱酰胺反应。该反应的 proposed 机制涉及形成一种酰亚胺中间体，该中间体裂解后导致氨基酸部分的释放。所描述的脱酰胺反应代表了第一个涉及非肽部分的化学模型，它模拟了在含有天冬酰胺或谷氨酰胺残基的蛋白质或肽中发生的生物和化学脱酰胺过程。