Intramolecular alpha-glucosaminidation: synthesis of mycothiol.
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.
Ajayi
Kehinde
K
Department of Chemistry and Chemical Biology, Rutgers-The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA.
Thakur
Vinay V
VV
Lapo
Robert C
RC
Knapp
Spencer
S
D002384:Catalysis; D003545:Cysteine / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007294:Inositol / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013865:Thioglycosides / Q000138:chemical synthesis / Q000737:chemistry
D006020:Glycopeptides; D013865:Thioglycosides; C089265:mycothiol; D007294:Inositol; D003545:Cysteine; D005944:Glucosamine