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Organic & Biomolecular Chemistry

The international home of synthetic, physical and biomolecular organic chemistry.




Paper

Org. Biomol. Chem., 2009, 7, 3128 - 3140, DOI: 10.1039/b907273j


Synthesis of a truncated bi-antennary complex-type N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases Endo A and Endo M

Thomas B. Parsons, James W. B. Moir and Antony J. Fairbanks


The synthesis of a truncated complex N-glycan hexasaccharide oxazoline was achieved producing a substrate that was assayed as an activated donor for glycosylation catalysed by the endohexosaminidases Endo A and Endo M. For Endo M competitive product hydrolysis was seen to limit synthetic efficiency. In spite of its natural hydrolytic selectivity wild type Endo A was able to process the truncated complex N-glycan oxazoline, albeit with limited synthetic efficiency; notably the product was not a substrate for Endo A catalysed hydrolysis. Two Endo A mutants, E173Q and E173H, were also assayed, but were unable to process this oxazoline.

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