Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1373243 | Bioorganic & Medicinal Chemistry Letters | 2007 | 4 Pages |
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. 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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jeet Kalia, Ronald T. Raines,