A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides

A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2025, Volume: 30, Number: 15, Article number : 3295, Pages count : DOI: 10.3390/molecules30153295

Authors

Abronina Polina I. ¹ , Malysheva Nelly N. ¹ , Karpenko Maxim Y. ¹ , Novikov Dmitry S. ¹ , Zinin Alexander I. ¹ , Kolotyrkina N.G. ¹ , Kononov Leonid O. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russia

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-β-(1→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.

Abronina P.I. , Malysheva N.N. , Karpenko M.Y. , Novikov D.S. , Zinin A.I. , Kolotyrkina N.G. , Kononov L.O.
A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides
Molecules. 2025. V.30. N15. 3295 . DOI: 10.3390/molecules30153295 WOS Scopus OpenAlex

Web of science:	WOS:001551064700001
Scopus:	2-s2.0-105013169436
OpenAlex:	W4413021504

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