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 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.
Chemistry Research Laboratory, Oxford University, Mansfield Road, Oxford OX1 3TA, UK.
Thomas W D F
TW
Rising
Timothy D W
TD
Claridge
Nicola
N
Davies
David P
DP
Gamblin
James W B
JW
Moir
Antony J
AJ
Fairbanks
D002240:Carbohydrate Sequence; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase / Q000378:metabolism*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000138:chemical synthesis*
D009844:Oligosaccharides; D010080:Oxazoles; D011134:Polysaccharides; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase