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Synthesis of a tetrasaccharide containing Janus aglycone related to the terminal fragment of polysaccharides of mycobacteria

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Abstract

A convergent synthesis of arabinofuranose-based, α-(1→5), β-(1→2)-linked tetrasaccharide related to the terminal fragment of lipoarabinomannan and arabinogalactan of mycobacteria was carried out. The tetrasaccharide was synthesized as a glycoside with 4-(2-azidoethoxy)phenyl aglycone belonging to the class of Janus aglycones, which can serve as both a temporary protective group of the anomeric position of the carbohydrate residue and a (pre)spacer for the synthesis of neoglycoconjugates (NGCs) useful in the development of new diagnostic agents for tuberculosis. The key step is the formation of a 1,2-cis-glycosidic bond.

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Authors and Affiliations

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

    P. I. Abronina, N. N. Malysheva, A. I. Zinin & L. O. Kononov

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  1. P. I. Abronina
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  2. N. N. Malysheva
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  3. A. I. Zinin
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  4. L. O. Kononov
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Correspondence to P. I. Abronina or L. O. Kononov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The authors acknowledge A. O. Chizhov and N. G. Kolotyrkina (both from the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences) for recording high-resolution mass spectra.

This work was financially supported by the Russian Science Foundation (Project No. 21-73-20164).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 1046–1058, April, 2023.

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Abronina, P.I., Malysheva, N.N., Zinin, A.I. et al. Synthesis of a tetrasaccharide containing Janus aglycone related to the terminal fragment of polysaccharides of mycobacteria. Russ Chem Bull 72, 1046–1058 (2023). https://doi.org/10.1007/s11172-023-3870-7

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