title: Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization.
abstract: The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging α-fucosylation and β-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a β-D-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.
authors: Complex Carbohydrate Research Center, The University of Georgia , 315 Riverbend Road, Athens, Georgia 30602, United States.
authors: Ivan A
authors: IA
authors: Gagarinov
authors: Tao
authors: T
authors: Fang
authors: Lin
authors: L
authors: Liu
authors: Apoorva D
authors: AD
authors: Srivastava
authors: Geert-Jan
authors: GJ
authors: Boons
mesh_terms: D006031:Glycosylation; D015394:Molecular Structure; D011135:Polysaccharides, Bacterial / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D013211:Staphylococcus aureus / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology
chemical_list: D011135:Polysaccharides, Bacterial; D014312:Trisaccharides