Catalysis of imido group hydrolysis in a maleimide conjugate

J Kalia, RT Raines

Index: Kalia, Jeet; Raines, Ronald T. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 22 p. 6286 - 6289

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Citation Number: 54

Abstract

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. ...