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

Thomas W. D. F. Rising; Timothy D. W. Claridge; Nicola Davies; David P. Gamblin; James W. B. Moir; Antony J. Fairbanks

doi:10.1016/j.carres.2006.03.007

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

Thomas W. D. F. Rising, Timothy D. W. Claridge, Nicola Davies, David P. Gamblin, James W. B. Moir, Antony J. Fairbanks

Biology

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	1574-1596
Number of pages	23
Journal	CARBOHYDRATE RESEARCH
Volume	341
Issue number	10
DOIs	https://doi.org/10.1016/j.carres.2006.03.007
Publication status	Published - 24 Jul 2006

Keywords

endoglycosidase
endohexosaminidase
oxazoline
N-glycan
transglycosylation
protein remodelling
SUBSTRATE-ASSISTED CATALYSIS
LINKED SUGAR CHAINS
CHEMOENZYMATIC SYNTHESIS
ACETYLGLUCOSAMINE MOIETIES
COMPLEX-TYPE
OLIGOSACCHARIDES
GLYCOPEPTIDES
TRANSGLYCOSYLATION
MANNOPYRANOSIDES
GLYCOPROTEINS

Access to Document

10.1016/j.carres.2006.03.007

Cite this

@article{02517c938a7843b9b55a013dde7f04c3,

title = "Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation",

abstract = "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.",

keywords = "endoglycosidase, endohexosaminidase, oxazoline, N-glycan, transglycosylation, protein remodelling, SUBSTRATE-ASSISTED CATALYSIS, LINKED SUGAR CHAINS, CHEMOENZYMATIC SYNTHESIS, ACETYLGLUCOSAMINE MOIETIES, COMPLEX-TYPE, OLIGOSACCHARIDES, GLYCOPEPTIDES, TRANSGLYCOSYLATION, MANNOPYRANOSIDES, GLYCOPROTEINS",

author = "Rising, {Thomas W. D. F.} and Claridge, {Timothy D. W.} and Nicola Davies and Gamblin, {David P.} and Moir, {James W. B.} and Fairbanks, {Antony J.}",

year = "2006",

month = jul,

day = "24",

doi = "10.1016/j.carres.2006.03.007",

language = "English",

volume = "341",

pages = "1574--1596",

journal = "CARBOHYDRATE RESEARCH",

issn = "0008-6215",

publisher = "Elsevier",

number = "10",

}

TY - JOUR

T1 - Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation

AU - Rising, Thomas W. D. F.

AU - Claridge, Timothy D. W.

AU - Davies, Nicola

AU - Gamblin, David P.

AU - Moir, James W. B.

AU - Fairbanks, Antony J.

PY - 2006/7/24

Y1 - 2006/7/24

N2 - 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.

AB - 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.

KW - endoglycosidase

KW - endohexosaminidase

KW - oxazoline

KW - N-glycan

KW - transglycosylation

KW - protein remodelling

KW - SUBSTRATE-ASSISTED CATALYSIS

KW - LINKED SUGAR CHAINS

KW - CHEMOENZYMATIC SYNTHESIS

KW - ACETYLGLUCOSAMINE MOIETIES

KW - COMPLEX-TYPE

KW - OLIGOSACCHARIDES

KW - GLYCOPEPTIDES

KW - TRANSGLYCOSYLATION

KW - MANNOPYRANOSIDES

KW - GLYCOPROTEINS

U2 - 10.1016/j.carres.2006.03.007

DO - 10.1016/j.carres.2006.03.007

M3 - Article

SN - 0008-6215

VL - 341

SP - 1574

EP - 1596

JO - CARBOHYDRATE RESEARCH

JF - CARBOHYDRATE RESEARCH

IS - 10

ER -