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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.

SUBMITTER: Ajayi K

PROVIDER: S-EPMC2892847 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Intramolecular alpha-glucosaminidation: synthesis of mycothiol.

Ajayi Kehinde K Thakur Vinay V VV Lapo Robert C RC Knapp Spencer S

Organic letters 20100601 11

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. ...[more]

PMID: 20443569

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