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; Antony J. Fairbanks

doi:10.1039/B907273J

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Organic & Biomolecular Chemistry

Issue 15, 2009

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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

Org. Biomol. Chem., 2009, 7, 3128-3140

DOI: 10.1039/B907273J
Received 09 Apr 2009, Accepted 13 May 2009
First published on the web 17 Jun 2009

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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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Spectra for compounds 1c–13
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Organic & Biomolecular Chemistry

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

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