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

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• 作者：Thomas W.D.F. Rising ; Timothy D.W. Claridge ; Nicola Davies ; David P. Gamblin ; James W.B. Moir and Antony J. Fairbanks
• 关键词：Endoglycosidase ; Endohexosaminidase ; Oxazoline ; N-Glycan ; Transglycosylation ; Protein remodelling
• 刊名：Carbohydrate Research
• 出版年：2006
• 出版时间：24 July 2006
• 年：2006
• 卷：341
• 期：10
• 页码：1574-1596
• 全文大小：635 K

文摘

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 β-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 β-d-GlcpNAcAsn glycosyl amino acid is demonstrated with the trisaccharide oxazoline donor.