title: Structures and Biosynthesis of Corvol Ethers--Sesquiterpenes from the Actinomycete Kitasatospora setae.
abstract: Here we present the functional characterization of a sesquiterpene cyclase from Kitasatospora setae. The enzyme converts the sesquiterpene precursor farnesyl diphosphate (FPP) into two previously unknown and unstable sesquiterpene ethers for which we propose the trivial names corvol ethers A and B. Both compounds were purified and their structures were determined by one- and two-dimensional NMR spectroscopy. A biosynthetic mechanism for the FPP cyclization by the corvol ether synthase was proposed. The results from the incubation experiments of the corvol ether synthase with isotopically labeled precursors were in line with this mechanism, while alternative mechanisms could clearly be ruled out.
authors: Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany); Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany).
authors: Patrick
authors: P
authors: Rabe
authors: Khomaizon A K
authors: KA
authors: Pahirulzaman
authors: Jeroen S
authors: JS
authors: Dickschat
mesh_terms: D019755:Carbon-Carbon Lyases / Q000737:chemistry / Q000378:metabolism*; D004987:Ethers / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D013306:Streptomycetaceae / Q000201:enzymology*
chemical_list: D004987:Ethers; D012717:Sesquiterpenes; D019755:Carbon-Carbon Lyases; C051130:trichodiene synthetase
keywords: NMR spectroscopy; biosynthesis; enzyme mechanisms; isotopic labeling; terpenoids