Synthesis of a hexasaccharide repeating unit from Bacillus anthracis vegetative cell walls.
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.
Oberli
Matthias A
MA
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, 8093 Zürich, Switzerland.
Bindschädler
Pascal
P
Werz
Daniel B
DB
Seeberger
Peter H
PH
D001408:Bacillus anthracis / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry*; D015394:Molecular Structure; D011135:Polysaccharides, Bacterial / Q000096:biosynthesis* / Q000737:chemistry
D011135:Polysaccharides, Bacterial