A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides
2025
Polina I. Abronina | Nelly N. Malysheva | Maxim Y. Karpenko | Dmitry S. Novikov | Alexander I. Zinin | N. G. Kolotyrkina | Leonid O. Kononov
A rational synthesis of the branched decaarabinofuranoside with 4-(2-azidoethoxy)phenyl aglycone (a Janus aglycone) related to the non-reducing terminal fragments of the arabinogalactan and lipoarabinomannan from Mycobacterium tuberculosis was proposed. Since the most challenging step is the formation of a 1,2-cis glycosidic linkage, we have significantly simplified access to a library of oligoarabinofuranosides derived from Mycobacterium tuberculosis polysaccharides using a silylated Ara-&beta:-(1&rarr:2)-Ara disaccharide as the glycosyl donor. The application of a Janus aglycone also allowed us to reduce the number of reaction steps in glycoside synthesis. The obtained arabinans can be useful to further prepare conjugates as antigens for creating tuberculosis screening assays.
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