Simplifying oligosaccharide synthesis: efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors.
A practical sequence is described for converting d-glucosamine into peracetylated Gal(beta-1,4)GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.
Yan
Fengyang
F
Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Room 3024, Ottawa, Ontario, K1A 0R6, Canada.
Mehta
Seema
S
Eichler
Eva
E
Wakarchuk
Warren W
WW
Gilbert
Michel
M
Schur
Melissa J
MJ
Whitfield
Dennis M
DM
D000606:Amino Sugars / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000606:Amino Sugars; D007202:Indicators and Reagents; D009844:Oligosaccharides; C032233:lactosamine