noviose has been researched along with clorobiocin* in 2 studies
2 other study(ies) available for noviose and clorobiocin
| Article | Year |
|---|---|
Biosynthesis of the unusual 5,5-gem-dimethyl-deoxysugar noviose: investigation of the C-methyltransferase gene cloU.
The aminocoumarin antibiotic clorobiocin contains an unusual branched deoxysugar with a 5,5-gem-dimethyl structure. Inactivation of the putative C-methyltransferase gene cloU was carried out, which led to the loss of the axial methyl group at C-5 of this deoxysugar moiety. This result establishes the function of cloU, and at the same time it proves that the biosynthesis of the deoxysugar moiety of clorobiocin proceeds via a 3,5-epimerization of the dTDP-4-keto-6-deoxyglucose intermediate. The inactivation was carried out on a cosmid which contained the entire clorobiocin biosynthetic gene cluster. Expression of the modified cluster in a heterologous host led to the formation of desmethyl-clorobiocin and a structural isomer thereof. Both compounds were isolated on a preparative scale, their structures were elucidated by 1H-NMR and mass spectroscopy and their antibacterial activity was assayed. Topics: Amino Acid Sequence; Anti-Bacterial Agents; Methyltransferases; Molecular Sequence Data; Monosaccharides; Novobiocin; Streptomyces | 2006 |
Metabolic engineering of aminocoumarins: inactivation of the methyltransferase gene cloP and generation of new clorobiocin derivatives in a heterologous host.
Aminocoumarin antibiotics are highly potent inhibitors of bacterial gyrase and represent a class of antibiotics that are very suitable for the generation of new compounds by metabolic engineering. In this study, the putative methyltransferase gene cloP in the biosynthetic gene cluster of clorobiocin was inactivated. Expression of the modified gene cluster in the heterologous host Streptomyces coelicolor M512 gave three new aminocoumarin antibiotics. The structures of the new compounds were elucidated by MS and 1H NMR, and their antibacterial activities were determined. All three compounds lacked clorobiocin's methyl group at 4-OH of the deoxysugar moiety, noviose. They differed from each other in the position of the 5-methylpyrrole-2-carbonyl group, which was found to be attached to either 2-OH, 3-OH or 4-OH of noviose. Attachment at 4-OH resulted in the highest antibacterial activity. This is the first time that an aminocoumarin antibiotic acylated at 4-OH in noviose has been detected. Topics: Acylation; Anti-Bacterial Agents; Antibiotics, Antineoplastic; Chromatography, High Pressure Liquid; Cosmids; Coumarins; Gene Targeting; Gene Transfer Techniques; Mass Spectrometry; Methyltransferases; Microbial Sensitivity Tests; Molecular Structure; Monosaccharides; Mutation; Novobiocin; Streptomyces coelicolor; Structure-Activity Relationship | 2005 |