Synthesis of a core arabinomannan oligosaccharide of Mycobacterium tuberculosis.
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.
Hölemann
Alexandra
A
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli-Strasse 10, HCI F 315, CH-8093 Zürich, Switzerland.
Stocker
Bridget L
BL
Seeberger
Peter H
PH
D009169:Mycobacterium tuberculosis / Q000737:chemistry*