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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

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Abstract

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.

Graphical abstract: 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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Publication details

The article was received on 09 Apr 2009, accepted on 13 May 2009 and first published on 17 Jun 2009


Article type: Paper
DOI: 10.1039/B907273J
Citation: Org. Biomol. Chem., 2009,7, 3128-3140
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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

    T. B. Parsons, J. W. B. Moir and A. J. Fairbanks, Org. Biomol. Chem., 2009, 7, 3128
    DOI: 10.1039/B907273J

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