Endohexosaminidase M: Exploring and Exploiting Enzyme Substrate Specificity

Abstract

Oxazoline saccharides have been synthesised and tested as glycosyl donors for endohexosaminidase M (Endo M)-catalysed glycosylation of a GlcNAcAsn glycosyl amino acid. Endo M-catalysed glycosylation is not limited to donors containing the Manβ(1-4)GlcNAc linkage, and replacement of the core mannose unit by glucose promotes irreversible glycosylation. In this case, use of a modified oxazoline donor as a transition-state mimic allows enzyme-catalysed synthesis, but precludes product hydrolysis.