Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation

被引：68

作者：

Rising, Thomas W. D. F.

Claridge, Timothy D. W.

Davies, Nicola

Gamblin, David P.

Moir, James W. B.

Fairbanks, Antony J.

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ York, Dept Biol, York YO10 5YW, N Yorkshire, England

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 10期

基金：

英国生物技术与生命科学研究理事会;

关键词：

endoglycosidase; endohexosaminidase; oxazoline; N-glycan; transglycosylation; protein remodelling;

D O I：

10.1016/j.carres.2006.03.007

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Oxazoline mono-, di-, tri- and hexasaccharides, corresponding to the core components of N-linked glycoprotein high mannose glycans, are synthesised as potential glycosyl donors for endohexosaminidase catalysed glycosylation of glycopeptides and glycoprotein remodelling. The crucial beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage is synthesised via epimerisation of gluco disaccharide substrates by sequential triflation and nucleophilic substitution. Oxazolines are formed directly from the anomeric OPMP protected N-acetyl glucosamine derivatives. Efficient endohexosaminidase catalysed glycosylation of a synthetic beta-D-GlcpNAcAsn glycosyl amino acid is demonstrated with the trisaccharide oxazoline donor. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1574 / 1596

页数：23

共 35 条

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