Diastereoselective synthesis of optically active (2 R,5 R)-hexanediol.

J Haberland, A Kriegesmann, E Wolfram, W Hummel, A Liese

Index: Appl. Microbiol. Biotechnol. 58(5) , 595-9, (2002)

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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.