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.


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