Catalysis of imido group hydrolysis in a maleimide conjugate
Catalysis of imido group hydrolysis in a maleimide conjugate
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DOI：
10.1016/j.bmcl.2007.09.002
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发表时间：
2007-11-15
影响因子：
2.7
通讯作者：
Raines, Ronald T.
中科院分区：
文献类型：
--
作者：
Kalia, Jeet;Raines, Ronald T.
马来酰亚胺通常用于与硫醇的生物分子缀合。马来酰亚胺缀合物中亚氨基的一个未被充分认识的方面是其对自发水解的敏感性，导致不期望的异质性。在这里，一个发色马来酰亚胺是用来证明，无论是钨酸盐和铬酸盐催化水解的亚氨基基团接近中性pH值。钨酸盐和4-（二甲氨基）吡啶是不太有效的催化剂。这项工作揭示了一种新的模式的化学反应性的马来酰亚胺和铬酸盐，并提供了一种策略，用于减少来自马来酰亚胺的生物共轭物的异质性。(C)2007爱思唯尔有限公司保留所有权利。
Maleimides are often used for biomolecular conjugation with thiols. An underappreciated aspect of the imido group in a maleimide conjugate is its susceptibility to spontaneous hydrolysis, resulting in undesirable heterogeneity. Here, a chromophoric maleimide is used to demonstrate that both molybdate and chromate catalyze the hydrolysis of an imido group near neutral pH. Tungstate and 4-(dimethylamino)pyridine are less effective as catalysts. This work reveals a new mode of chemical reactivity for molybdate and chromate, and provides a strategy for decreasing the heterogeneity of bioconjugates derived from maleimides. (C) 2007 Elsevier Ltd. All rights reserved.