title: Pristinol, a Sesquiterpene Alcohol with an Unusual Skeleton from Streptomyces pristinaespiralis.
abstract: A terpene cyclase from Streptomyces pristinaespiralis was characterized as the synthase for (+)-(2S,3S,9R)-pristinol. The structure of this sesquiterpene alcohol, which has a new carbon skeleton, was established by NMR spectroscopy and single-wavelength anomalous-dispersion X-ray crystallography. Extensive isotopic labelling experiments were performed to distinguish between various possible cyclization mechanisms of the terpene cyclase and to decipher the EI-MS fragmentation mechanism for pristinol.
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany.
authors.forename: Tim A
authors.initials: TA
authors.lastname: Klapschinski
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany.
authors.forename: Patrick
authors.initials: P
authors.lastname: Rabe
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany. dickschat@uni-bonn.de.
authors.forename: Jeroen S
authors.identifier: 0000-0002-0102-0631
authors.initials: JS
authors.lastname: Dickschat
mesh_terms: D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D012717:Sesquiterpenes; C000628191:pristinol
keywords: NMR spectroscopy; enzyme mechanisms; isotopic labelling; mass spectrometry; terpenes