Intramolecular alpha-glucosaminidation: synthesis of mycothiol.

Abstract	A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively alpha-selective intramolecular glycosylation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.
Authors	Kehinde Ajayi, Vinay V Thakur, Robert C Lapo, Spencer Knapp
Journal	Organic letters (Org Lett) Vol. 12 Issue 11 Pg. 2630-3 (Jun 04 2010) ISSN: 1523-7052 [Electronic] United States
PMID	20443569 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov't, Non-P.H.S.)
Chemical References	Glycopeptides Thioglycosides mycothiol Inositol Cysteine Glucosamine
Topics	Catalysis Cysteine (chemical synthesis, chemistry) Glucosamine (chemistry) Glycopeptides (chemical synthesis, chemistry) Glycosylation Inositol (chemical synthesis, chemistry) Molecular Structure Mycobacterium tuberculosis (chemistry) Nuclear Magnetic Resonance, Biomolecular Stereoisomerism Thioglycosides (chemical synthesis, chemistry)

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