title: Simplifying oligosaccharide synthesis: efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors.
abstract: 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.
authors.affiliation: Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Room 3024, Ottawa, Ontario, K1A 0R6, Canada.
authors.forename: Fengyang
authors.initials: F
authors.lastname: Yan
authors.forename: Seema
authors.initials: S
authors.lastname: Mehta
authors.forename: Eva
authors.initials: E
authors.lastname: Eichler
authors.forename: Warren W
authors.initials: WW
authors.lastname: Wakarchuk
authors.forename: Michel
authors.initials: M
authors.lastname: Gilbert
authors.forename: Melissa J
authors.initials: MJ
authors.lastname: Schur
authors.forename: Dennis M
authors.initials: DM
authors.lastname: Whitfield
mesh_terms: 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
chemical_list: D000606:Amino Sugars; D007202:Indicators and Reagents; D009844:Oligosaccharides; C032233:lactosamine