Catalysis of imido group hydrolysis in a maleimide conjugate.
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.
Kalia
Jeet
J
Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706, USA.
Raines
Ronald T
RT
D002384:Catalysis; D002840:Chromates / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007094:Imides / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry
D002840:Chromates; D007094:Imides; D008301:Maleimides; C044659:molybdate; C043592:maleimide; D008982:Molybdenum