title: Synthesis of a hexasaccharide repeating unit from Bacillus anthracis vegetative cell walls.
abstract: The first synthesis of hexasaccharide 1 representing a repeat unit of a polysaccharide specific to the vegetative cell wall of Bacillus anthracis is reported. The synthetic hexasaccharide is equipped with an n-pentenyl handle at the reducing terminus to allow for further functionalization. Key transformations during the synthesis are the conversion of a glucose into a mannosazide residue, a (2+2) coupling, followed by double alpha-galactosylation to furnish the hexasaccharide, and global deprotection under Birch conditions.
authors.affiliation: Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, 8093 Zürich, Switzerland.
authors.forename: Matthias A
authors.initials: MA
authors.lastname: Oberli
authors.forename: Pascal
authors.initials: P
authors.lastname: Bindschädler
authors.forename: Daniel B
authors.initials: DB
authors.lastname: Werz
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D001408:Bacillus anthracis / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry*; D015394:Molecular Structure; D011135:Polysaccharides, Bacterial / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D011135:Polysaccharides, Bacterial