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

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-Man p-(1→4)-...

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Bibliographic Details
Published in:Carbohydrate research 2006-07, Vol.341 (10), p.1574-1596
Main Authors: Rising, Thomas W.D.F., Claridge, Timothy D.W., Davies, Nicola, Gamblin, David P., Moir, James W.B., Fairbanks, Antony J.
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Endoglycosidase
Endohexosaminidase
Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase - metabolism
Molecular Sequence Data
N-Glycan
Oligosaccharides - chemical synthesis
Oxazoles - chemical synthesis
Oxazoline
Polysaccharides - chemical synthesis
Protein remodelling
Transglycosylation
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Summary: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-Man p-(1→4)- d-Glc pNAc 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-Glc pNAcAsn glycosyl amino acid is demonstrated with the trisaccharide oxazoline donor.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2006.03.007