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
Publisher: American Chemical Society
: 2024
: Organic Letters
: Organic Letters
: 26
: 10
: 2034
: 2038
: 1523-7060
: 1523-7052
DOI: https://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.