A1 Refereed original research article in a scientific journal

Synthesis of an Immunologically Active Heptamannoside of Mycobacterium tuberculosis by the [Au]/[Ag]-Catalyzed Activation of Ethynylcyclohexyl Glycosyl Carbonate Donor




AuthorsShinde Ganesh P., Sutar Yogesh, Kasdekar Niteshlal, Joshi Pooja, Rasool Omid, Ignatowicz Lech, Hamasur Beston, Hotha Srinivas

PublisherAmerican Chemical Society

Publication year2024

JournalOrganic Letters

Journal name in sourceOrganic Letters

Volume26

Issue10

First page 2034

Last page2038

ISSN1523-7060

eISSN1523-7052

DOIhttps://doi.org/10.1021/acs.orglett.4c00175

Web address https://pubs.acs.org/doi/abs/10.1021/acs.orglett.4c00175

Self-archived copy’s web addresshttps://research.utu.fi/converis/portal/detail/Publication/387288828


Abstract

Tuberculosis (TB) is one of the most dreadful diseases, killing more than 3 million humans annually. M. tuberculosis (MTb) is the causative agent for TB and has a thick and waxy cell wall, making it an attractive target for immunological studies. In this study, a heptamannopyranoside containing 1 → 2 and 1 → 6 α-mannopyranosidic linkages has been explored for the immunological evaluations. The conjugation-ready heptamannopyranoside was synthesized by exploiting the salient features of recently discovered [Au]/[Ag]-glycosidation of ethynylcyclohexyl glycosyl carbonate donors. The glycan was conjugated to the ESAT6, an early secreted protein of MTb for further characterization as a potential subunit vaccine candidate. © 2024 American Chemical Society.


Downloadable publication

This is an electronic reprint of the original article.
This reprint may differ from the original in pagination and typographic detail. Please cite the original version.





Last updated on 2025-06-03 at 08:36