title: Synthesis of a core arabinomannan oligosaccharide of Mycobacterium tuberculosis.
abstract: The synthesis of a core arabinomannan (AM) oligosaccharide from Mycobacterium tuberculosis has been achieved using a convergent [6 + 6] glycosylation strategy and a defined set of building blocks. Dodecasaccharide 1, containing the key AM structural features of lipoarabinomannan (LAM), was obtained in excellent yield and selectivity from hexamannan 3 and hexaarabinan 5. This flexible synthetic strategy involves late-stage couplings and modifications, thus providing ready access to several different LAM fragments. The incorporation of a thiol linker at the reducing end of the oligosaccharide allows for the attachment of these compounds to microarrays and protein carriers.
authors.affiliation: Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli-Strasse 10, HCI F 315, CH-8093 Zürich, Switzerland.
authors.forename: Alexandra
authors.initials: A
authors.lastname: Hölemann
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D009169:Mycobacterium tuberculosis / Q000737:chemistry*