Diastereoselective synthesis of optically active (2 R,5 R)-hexanediol.
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.
Haberland
J
J
Forschungszentrum Jülich GmbH, Institute of Biotechnology, 52425 Jülich, Germany.
Kriegesmann
A
A
Wolfram
E
E
Hummel
W
W
Liese
A
A
D006018:Glycols / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D019344:Lactic Acid / Q000096:biosynthesis / Q000378:metabolism; D007778:Lactobacillus / Q000378:metabolism*; D013237:Stereoisomerism
D006018:Glycols; C007938:2,5-hexanediol; D019344:Lactic Acid