Work

Intramolecular α-Glucosaminidation: Synthesis of Mycothiol

Year: 2010

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol1008334

Authors: Kehinde Ajayi, Vinay V. Thakur, Robert C. Lapo, Spencer Knapp

Institution: Rutgers, The State University of New Jersey

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of Allergy and Infectious Diseases

Awards: Inhibition of Tubercular Mycothiol Pathways, G5060013164