Asymmetric reduction of benzil to (S)-benzoin with whole cells of Bacillus cereus.
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).
Saito
Tomoya
T
Department of System Engineering of Materials and Life Sciences, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan.
Maruyama
Reiji
R
Ono
Shin
S
Yasukawa
Nobuo
N
Kodaira
Ken-ichi
K
Nishizawa
Mikio
M
Ito
Seiji
S
Inoue
Masami
M
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
D002021:Buffers; D003470:Culture Media; D005947:Glucose; D001573:Benzoin; D010658:Phenylglyoxal; C006697:benzil