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 Lettjournal_title
Bioorganic & medicinal chemistry lettersauthors
Kalia J,Raines RTdoi
10.1016/j.bmcl.2007.09.002subject
Has Abstractpub_date
2007-11-15 00:00:00pages
6286-9issue
22eissn
0960-894Xissn
1464-3405pii
S0960-894X(07)01034-7journal_volume
17pub_type
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