Shortcut to mycothiol analogues.
[structure: see text] The synthesis of a simplified thioglycosidic analogue (2) of mycothiol (1) is described. Evaluation of 2 against mycothiol S-conjugate amidase from Mycobacterium tuberculosis reveals good specific activity (7500 nmol min(-)(1) mg-protein(-)(1), vs 14 200 for 1), indicating that 2 can serve as a starting point for antitubercular drug design.
Knapp
Spencer
S
Department of Chemistry and Chemical Biology, Rutgers The State University of New Jersey, 610 Taylor Rd., Piscataway, New Jersey 08854-8087, USA. knapp@rutchem.rutgers.edu
Gonzalez
Silvia
S
Myers
David S
DS
Eckman
Lisa L
LL
Bewley
Carole A
CA
D000581:Amidohydrolases / Q000378:metabolism; D000995:Antitubercular Agents / Q000737:chemistry* / Q000378:metabolism*; D003545:Cysteine; D004187:Disaccharides / Q000096:biosynthesis* / Q000737:chemistry* / Q000378:metabolism; D015195:Drug Design; D006020:Glycopeptides; D007294:Inositol; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000201:enzymology; D011720:Pyrazoles / Q000737:chemistry* / Q000378:metabolism; D013438:Sulfhydryl Compounds / Q000737:chemistry* / Q000378:metabolism
D000995:Antitubercular Agents; D004187:Disaccharides; D006020:Glycopeptides; D011720:Pyrazoles; D013438:Sulfhydryl Compounds; C089265:mycothiol; D007294:Inositol; D000581:Amidohydrolases; C413523:mycothiol S-conjugate amidase; D003545:Cysteine