Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the Mycobacterium tuberculosis cellular envelope by glycosyl carbonate donors

Chemical Science
Maidul IslamSrinivas Hotha

Abstract

The global incidence of tuberculosis is increasing at an alarming rate, and Mycobacterium tuberculosis (Mtb) is the causative agent for tuberculosis, a disease with high mortality. Lipoarabinomannan (LAM) is one of the major components of the Mtb cellular envelope and is an attractive scaffold for developing anti-tubercular drugs, vaccines and diagnostics. Herein, a highly convergent strategy is developed to synthesize heneicosasaccharyl arabinomannan for the first time. The arabinomannan synthesized in this endeavour has several 1,2-trans or α-Araf linkages and three 1,2-cis or β-Araf linkages end capped with 1,2-trans or α-Manp linkages. All the key glycosidations were performed with alkynyl carbonate glycosyl donors under [Au]/[Ag] catalysis conditions, which gave excellent yields and stereoselectivity even for the reactions between complex and branched oligosaccharides. The resultant allyl oligosaccharide was globally deprotected to obtain the heneicosasaccharyl arabinomannan as a propyl glycoside. In summary, heneicosasaccharyl mannose capped arabinomannan synthesis was achieved in 56 steps with 0.016% overall yield.

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Citations

Aug 2, 2017·Chemical Communications : Chem Comm·K NareshP H Seeberger
Dec 17, 2019·Beilstein Journal of Organic Chemistry·Alonso Pardo-VargasPeter H Seeberger
Apr 7, 2018·Journal of the American Chemical Society·Martina DelbiancoPeter H Seeberger
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Giulio FittolaniMartina Delbianco
Oct 7, 2017·The Journal of Organic Chemistry·Mahesh NeralkarSrinivas Hotha
Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung
Sep 10, 2019·ACS Omega·Pablo ValverdeJesús Jiménez-Barbero

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Methods Mentioned

BETA
glycosidation
column chromatography
NMR
glycosylations

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