title: Synthesis of 1-D- and 1-L-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside establishes substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase.
abstract: Mycothiol (MSH, 1-D-myo-inosityl 2-(N-acetyl-L-cysteinyl)amido-2-deoxy-alpha-D-glucopyranoside) is the principal low molecular weight thiol in actinomycetes. The enzyme 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase (AcGI deacetylase) is involved in the biosynthesis of MSH and forms the free amine 1-D-myo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside, which is used in the third of four steps of MSH biosynthesis. Here, we report the synthesis of two isomers of AcGI, which contain either 1-L-myo-inositol or 1-D-myo-inositol. These synthetic products were used to investigate substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase.
authors.affiliation: Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892-0820, USA.
authors.forename: Gillian M
authors.initials: GM
authors.lastname: Nicholas
authors.forename: Lisa L
authors.initials: LL
authors.lastname: Eckman
authors.forename: Pavol
authors.initials: P
authors.lastname: Kovác
authors.forename: Sarah
authors.initials: S
authors.lastname: Otero-Quintero
authors.forename: Carole A
authors.initials: CA
authors.lastname: Bewley
mesh_terms: D000581:Amidohydrolases / Q000378:metabolism*; D001426:Bacterial Proteins; D003545:Cysteine; D004187:Disaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D006020:Glycopeptides; D007294:Inositol; D009169:Mycobacterium tuberculosis / Q000201:enzymology*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000378:metabolism; D011993:Recombinant Fusion Proteins / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000378:metabolism
chemical_list: D001426:Bacterial Proteins; D004187:Disaccharides; D006020:Glycopeptides; D011720:Pyrazoles; D011993:Recombinant Fusion Proteins; D013438:Sulfhydryl Compounds; C089265:mycothiol; D007294:Inositol; D000581:Amidohydrolases; C417275:N-acetyl-1-D-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside deacetylase; D003545:Cysteine