title: First synthesis of Bacillus cereus Ch HF-PS cell wall trisaccharide repeating unit.
abstract: The first total synthesis of Ch HF-PS, a cell wall trisaccharide repeating unit of B. cereus, is reported. The synthetic trisaccharide is appended with an aminopropyl linker at the reducing end to allow for conjugation to proteins and microarrays. The convergent synthesis involves transformation of d-mannose into an orthogonally protected rare AAT sugar building block, two consecutive α-stereoselective glycosylations, β-selective attachment of the linker by solvent participation, and amide bond formation, as key steps.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay , Mumbai 400076, India.
authors.forename: Ananda Rao
authors.initials: AR
authors.lastname: Podilapu
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
mesh_terms: D001409:Bacillus cereus / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry*; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011135:Polysaccharides, Bacterial / Q000138:chemical synthesis* / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000597815:Ch HF-PS; D011135:Polysaccharides, Bacterial; D014312:Trisaccharides; D008358:Mannose