title: First total synthesis of mycothiol and mycothiol disulfide.
abstract: [reaction: see text] The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-alpha,beta-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.
authors.affiliation: Division of Medicinal and Natural Products Chemistry, College of Pharmacy, and Center for Biocatalysis and Bioprocessing, The University of Iowa, Iowa City, Iowa 52242, USA.
authors.forename: Sungwon
authors.initials: S
authors.lastname: Lee
authors.forename: John P N
authors.initials: JP
authors.lastname: Rosazza
mesh_terms: D003545:Cysteine / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry; D006020:Glycopeptides; D007294:Inositol / Q000737:chemistry; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004187:Disaccharides; D006020:Glycopeptides; D011720:Pyrazoles; D013438:Sulfhydryl Compounds; C089265:mycothiol; D007294:Inositol; D003545:Cysteine; D005944:Glucosamine