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Synthesis of 4-(3-azidopropoxy)phenyl glycoside of tetraarabinofuranoside related to the terminal fragment of arabinogalactan and lipoarabinomannan of mycobacteria

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Abstract

A convergent synthesis of tetraarabinofuranoside β-d-Araf-(1→2)-α-d-Araf-(1→3)-α-d-Araf-(1→5)-α-d-Araf-1↑OR (R is 4-(3-azidopropoxy)phenyl) related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria was developed. The synthesized tetraarabinofuranoside represents a linear motif of a branched hexaarabinofuranoside, which is the main LAM epitope. 4-(3-Azidopropoxy)phenyl aglycone belongs to the class of Janus aglycones, which can serve as both a temporary protective group for the anomeric position of carbohydrate and a (pre)spacer for the synthesis of neoglycoconjugates useful for the development of new tuberculosis diagnostic assays. The key step of the synthesis is the formation of 1,2-cis-glycosidic bond.

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Acknowledgments

The authors are grateful to A. O. Chizhov and N. G. Kolotyrkina (both from N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences) for performing high-resolution mass spectrometry.

Funding

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

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

    P. I. Abronina, M. Yu. Karpenko, N. N. Malysheva, A. I. Zinin, I. V. Myachin & L. O. Kononov

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 1, pp. 189–203, January, 2024.

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Abronina, P.I., Karpenko, M.Y., Malysheva, N.N. et al. Synthesis of 4-(3-azidopropoxy)phenyl glycoside of tetraarabinofuranoside related to the terminal fragment of arabinogalactan and lipoarabinomannan of mycobacteria. Russ Chem Bull 73, 189–203 (2024). https://doi.org/10.1007/s11172-024-4131-z

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