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Development of an Orthogonal Protection Strategy for the Synthesis of Mycobacterial Arabinomannan Fragments
journal contribution
posted on 2015-11-20, 00:00 authored by Kamar Sahloul, Todd L. LowaryMycobacterium tuberculosis, the organism that
causes tuberculosis (TB), has a carbohydrate-rich cell wall structure
that possesses a number of immunogenic antigens. Circulating antibodies
that recognize these glycans are present in patients infected by mycobacteria;
detection of these antibodies could be the basis for new TB diagnostics.
We describe here the synthesis of a panel of mycobacterial arabinomannan
fragments for use in investigations directed at testing the feasibility
of such a diagnostic method. In this study, we focused on structural
motifs present in the core of the key immunogenic polysaccharide lipoarabinomannan
(LAM). To access these compounds, we developed an efficient orthogonal
protection strategy that allowed access to seven arabinomannan fragments
of LAM (1–7). The targets included
one tetrasaccharide, one pentasaccharide, three octasaccharides, and
two nonasaccharides. Starting from a differentially protected trimannopyranoside
derivative (8 or 9), the targets were obtained
using an approach that involved selective removal of the protecting
group present at the O-2 position of a single mannopyranoside residue,
followed by glycosylation with a pentaarabinofuranose thioglycoside
and/or a mannopyranose trichloroacetimidate.
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Orthogonal Protection Strategyarabinomannan fragmentsmycobacterial arabinomannan fragmentsremovalSynthesioctasaccharidetrimannopyranosidecompoundLAMMycobacterial Arabinomannan FragmentsMycobacterium tuberculosisapproachTB diagnosticsdifferentiallytestingdetectionorthogonal protection strategyglycosylationaccessinvestigationmethodpentaarabinofuranose thioglycosidecoreimmunogenic antigenspanelantibodynonasaccharidebasistetrasaccharidesynthesisfeasibilitycauses tuberculosismotifpentasaccharidemannopyranoside residuemannopyranose trichloroacetimidateCirculating antibodiesimmunogenic polysaccharide lipoarabinomannanglycanorganism
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