title: A detailed view on 1,8-cineol biosynthesis byStreptomyces clavuligerus.
abstract: The stereochemical course of the cyclisation reaction catalysed by the bacterial 1,8-cineol synthase fromStreptomyces clavuligeruswas investigated using stereospecifically deuterated substrates. In contrast to the well investigated plant enzyme fromSalvia officinalis, the reaction proceeds via (S)-linalyl diphosphate and the (S)-terpinyl cation, while the final cyclisation reaction is in both cases asynaddition, as could be shown by incubation of (2-13C)geranyl diphosphate in deuterium oxide.
authors.affiliation: Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Rinkel
authors.affiliation: Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Patrick
authors.initials: P
authors.lastname: Rabe
authors.affiliation: Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Laura
authors.initials: L
authors.lastname: Zur Horst
authors.affiliation: Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Jeroen S
authors.initials: JS
authors.lastname: Dickschat
keywords: biosynthesis; enzyme mechanisms; isotopic labelling; stereochemistry; terpenes