Catalysis of imido group hydrolysis in a maleimide conjugate

[摘要] 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.

[发布日期] 2007-11-15

[关键词] bioconjugation;catalysis;chromate;hydrolysis;imido group;malemide;molybdate;oxometalate;succinimide