title: Enantiospecific (S)-(+)-linalool formation from beta-myrcene by linalool dehydratase-isomerase.
abstract: The linalool dehydratase-isomerase from Castellaniella defragrans strain 65Phen catalyzes in the thermodynamically unfavourable direction the hydration of betamyrcene to linalool and further the isomerization to geraniol, the initial steps in anaerobic beta-myrcene biodegradation. We have now investigated the stereochemistry of this reaction. (S)-(+)-Linalool is formed with an enantiomeric excess of at least 95.4%. (R)-(-)-Linalool was not detected. This indicates an introduction of the hydroxy group on the si-face of beta-myrcene.
authors.affiliation: Department of Microbiology, Max Planck Institute for Marine Microbiology, Celsiusstr. 1, D-28359 Bremen, Germany.
authors.forename: Frauke
authors.initials: F
authors.lastname: Lüddeke
authors.forename: Jens
authors.initials: J
authors.lastname: Harder
mesh_terms: D000080462:Acyclic Monoterpenes; D001711:Biotransformation; D002384:Catalysis; D006836:Hydro-Lyases / Q000737:chemistry / Q000378:metabolism*; D039821:Monoterpenes / Q000378:metabolism*; D020560:Proteobacteria / Q000201:enzymology*; D013237:Stereoisomerism
chemical_list: D000080462:Acyclic Monoterpenes; D039821:Monoterpenes; C008574:beta-myrcene; C018584:linalool; D006836:Hydro-Lyases; C561837:linalool dehydratase-isomerase, Castellaniella defragrans