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




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

PublisherAmerican Chemical Society

2024

Organic Letters

Organic Letters

26

10

2034

2038

1523-7060

1523-7052

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

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

https://research.utu.fi/converis/portal/detail/Publication/387288828



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.


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