title: A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides.
abstract: Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the method with the formation of a pentasaccharide. The key building block is an orthogonally protected N-trifluoroacetamido thioglycoside donor that was added in succession to a glycosyl acceptor, enabling efficient glycosylation of the growing chain. In the second step of the iterative cycle, this building block is quantitatively deprotected at the C-6-hydroxyl position, ready for the next saccharide addition. Building from an azido-functionalised GlcNAc monosaccharide acceptor, the pentasaccharide was synthesised in seven steps in an overall yield of 25%.
authors.affiliation: The School of Chemistry and Molecular Biosciences, University of Queensland, St Lucia, QLD 4072, Australia.
authors.forename: Lucy G
authors.initials: LG
authors.lastname: Weaver
authors.forename: Yogendra
authors.initials: Y
authors.lastname: Singh
authors.forename: Joanne T
authors.initials: JT
authors.lastname: Blanchfield
authors.forename: Paul L
authors.initials: PL
authors.lastname: Burn
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D018441:Biofilms; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013211:Staphylococcus aureus / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D013865:Thioglycosides; C113831:poly-N-acetyl glucosamine; D005944:Glucosamine; D000117:Acetylglucosamine