title: Asymmetric reduction of benzil to (S)-benzoin with whole cells of Bacillus cereus.
abstract: Benzil (1) was selectively reduced to (S)-benzoin (2) in the presence of a wild-type Bacillus cereus Tim-r01. A 92% yield of 2 with 94% enantiomeric excess ratio was attained in phosphate-buffered saline (PBS) (pH 7.5) by using glucose as a nutrient at 37 degrees C for 12 h. Compound 2 was not reduced further to hydrobenzoin (3) at all. The reduction activity differed greatly depending on the strain of B. cereus. Under these conditions the B. cereus strains IFO3001, IFO15305, IAM1110, IAM1229, IAM1656, and IAM1729 gave 2 in yields ranging from 23 to 46% and the configuration of 2 was (S)-form (7 to 86% ee).
authors.affiliation: Department of System Engineering of Materials and Life Sciences, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Saito
authors.forename: Reiji
authors.initials: R
authors.lastname: Maruyama
authors.forename: Shin
authors.initials: S
authors.lastname: Ono
authors.forename: Nobuo
authors.initials: N
authors.lastname: Yasukawa
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Kodaira
authors.forename: Mikio
authors.initials: M
authors.lastname: Nishizawa
authors.forename: Seiji
authors.initials: S
authors.lastname: Ito
authors.forename: Masami
authors.initials: M
authors.lastname: Inoue
mesh_terms: D001409:Bacillus cereus / Q000201:enzymology* / Q000235:genetics; D001573:Benzoin / Q000737:chemistry* / Q000378:metabolism; D002021:Buffers; D003470:Culture Media; D005947:Glucose / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D010084:Oxidation-Reduction; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013696:Temperature; D013997:Time Factors
chemical_list: D002021:Buffers; D003470:Culture Media; D005947:Glucose; D001573:Benzoin; D010658:Phenylglyoxal; C006697:benzil