Catalysis of imido group hydrolysis in a maleimide conjugate.

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.

journal_name

Bioorg Med Chem Lett

authors

Kalia J,Raines RT

doi

10.1016/j.bmcl.2007.09.002

subject

Has Abstract

pub_date

2007-11-15 00:00:00

pages

6286-9

issue

22

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(07)01034-7

journal_volume

17

pub_type

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