title: De novo synthesis of the bacterial 2-amino-2,6-dideoxy sugar building blocks D-fucosamine, D-bacillosamine, and D-xylo-6-deoxy-4-ketohexosamine.
abstract: The cell-surface glycans on bacteria contain many monosaccharides that cannot be obtained by isolation from natural sources. Availability of differentially protected monosaccharides is therefore often limiting access to potential oligosaccharide vaccine antigens. D-Fucosamine, D-bacillosamine, and D-xylo-2,6-deoxy-4-ketohexosamine building blocks were prepared via a divergent de novo synthesis from L-Garner aldehyde. The route relies on a chelation-control assisted organometallic addition and an anti-selective dihydroxylation reaction.
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
authors.forename: Daniele
authors.initials: D
authors.lastname: Leonori
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006595:Hexosamines; D009005:Monosaccharides; D011134:Polysaccharides; C048215:2-fucosamine; D005643:Fucose; C013920:4-deoxyneosamine C