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.
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Rising et al. (2006) studied this question.
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