Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 17, Issue 22, Pages 6286-6289Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2007.09.002
Keywords
bioconjugation; catalysis; chromate; hydrolysis; imido group; malemide; molybdate; oxometalate; succinimide
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Funding
- NIGMS NIH HHS [R01 GM044783-16, R01 GM044783, GM 44783] Funding Source: Medline
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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.
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