title: Diastereoselective synthesis of optically active (2 R,5 R)-hexanediol.
abstract: Diastereoselective reduction of diketones with Lactobacillus kefir DSM 20587 was examined. The reduction of both oxo-functions proceeded highly diastereoselectively. (2 R,5 R)-Hexanediol 3 was produced starting from (2,5)-hexanedione 1 in quantitative yields with enantiomeric excess >99% and diastereomeric excess >99%. The reaction conditions were optimized: maximum yield of (2 R,5 R)-hexanediol was reached at pH 6, 30 degrees C and with equal amounts of substrate and cosubstrate. The applicability of the system in fed-batch experiments was demonstrated. The feed specific biomass concentration required to reach maximal yield and selectivity in fed-batch mode was determined.
authors.affiliation: Forschungszentrum Jülich GmbH, Institute of Biotechnology, 52425 Jülich, Germany.
authors.forename: J
authors.initials: J
authors.lastname: Haberland
authors.forename: A
authors.initials: A
authors.lastname: Kriegesmann
authors.forename: E
authors.initials: E
authors.lastname: Wolfram
authors.forename: W
authors.initials: W
authors.lastname: Hummel
authors.forename: A
authors.initials: A
authors.lastname: Liese
mesh_terms: D006018:Glycols / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D019344:Lactic Acid / Q000096:biosynthesis / Q000378:metabolism; D007778:Lactobacillus / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D006018:Glycols; C007938:2,5-hexanediol; D019344:Lactic Acid