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Volume 31
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10.3390/molecules31101598
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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Super-Armed Thiomannopyranosides in the Synthesis of a Mannose-Capped Trisaccharide of Mycobacterium tuberculosis Lipoarabinomannan

by
Polina Igorevna Abronina
*,
Zinaida Vladimirovna Kuznetsova
,
Dmitry Sergeevich Novikov
,
Alexander Ivanovich Zinin
,
Natalya G. Georgievna Kolotyrkina
and
Leonid Olegovich Kononov
*
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, Moscow 119991, Russia
*
Authors to whom correspondence should be addressed.
Molecules 2026, 31(10), 1598; https://doi.org/10.3390/molecules31101598
Submission received: 1 April 2026 / Revised: 5 May 2026 / Accepted: 7 May 2026 / Published: 10 May 2026
(This article belongs to the Special Issue 30th Anniversary of Molecules—Recent Advances in Organic Chemistry)
Review Reports Versions Notes

Abstract

Silylation of phenyl 1-thio-α-d-mannopyranoside, ethyl 1-thio-α- and β-d-mannopyranosides under different conditions was studied. Low-temperature NMR analysis revealed that the silylated products typically exist as an equilibrium of two chair conformations with a predominance of the axially rich 1C4 conformation. The dependence of the ratio of conformers on the anomeric configuration, the type of silyl groups and the nature of the aglycone was established. The fully silylated phenyl 1-thio-α-d-mannopyranoside, ethyl 1-thio-α- and β-d-mannopyranosides were tested as glycosyl donors in the synthesis of di- and trisaccharides, including one-pot synthesis. In all cases, only a-linked oligosaccharides as mixtures of conformers were formed. The obtained deprotected Manp-(1→2)-α-d-Manp-(1→5)-α-d-Araf trisaccharide 2-azidoethyl glycoside, related to the non-reducing terminal fragment of the mannose-capped lipoarabinomannan (ManLAM) of Mycobacterium tuberculosis, can be used for further preparation of conjugates with proteins to provide antigens, which are important for development of new tuberculosis screening assays.
Keywords: glycosylation; d-arabinofuranose; d-mannopyranose; silyl group; Mycobacterium tuberculosis; one pot synthesis glycosylation; d-arabinofuranose; d-mannopyranose; silyl group; Mycobacterium tuberculosis; one pot synthesis

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MDPI and ACS Style

Abronina, P.I.; Kuznetsova, Z.V.; Novikov, D.S.; Zinin, A.I.; Kolotyrkina, N.G.G.; Kononov, L.O. Super-Armed Thiomannopyranosides in the Synthesis of a Mannose-Capped Trisaccharide of Mycobacterium tuberculosis Lipoarabinomannan. Molecules 2026, 31, 1598. https://doi.org/10.3390/molecules31101598

AMA Style

Abronina PI, Kuznetsova ZV, Novikov DS, Zinin AI, Kolotyrkina NGG, Kononov LO. Super-Armed Thiomannopyranosides in the Synthesis of a Mannose-Capped Trisaccharide of Mycobacterium tuberculosis Lipoarabinomannan. Molecules. 2026; 31(10):1598. https://doi.org/10.3390/molecules31101598

Chicago/Turabian Style

Abronina, Polina Igorevna, Zinaida Vladimirovna Kuznetsova, Dmitry Sergeevich Novikov, Alexander Ivanovich Zinin, Natalya G. Georgievna Kolotyrkina, and Leonid Olegovich Kononov. 2026. "Super-Armed Thiomannopyranosides in the Synthesis of a Mannose-Capped Trisaccharide of Mycobacterium tuberculosis Lipoarabinomannan" Molecules 31, no. 10: 1598. https://doi.org/10.3390/molecules31101598

APA Style

Abronina, P. I., Kuznetsova, Z. V., Novikov, D. S., Zinin, A. I., Kolotyrkina, N. G. G., & Kononov, L. O. (2026). Super-Armed Thiomannopyranosides in the Synthesis of a Mannose-Capped Trisaccharide of Mycobacterium tuberculosis Lipoarabinomannan. Molecules, 31(10), 1598. https://doi.org/10.3390/molecules31101598

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