Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by fungi.
The enantioselectivity of ECAA to ECHB by eight fungi of four genus was evaluated. All strains showed (S)-selectivity, and Cylindrocarpon sclerotigenum IFO 31855 gave the highest yield and good optical purity (e.e.; >99%). Cell-free extract and acetone-dried cells of C. sclerotigenum IFO 31855 reduced ECAA to (S)-ECHB in the presence of NADPH (e.e.; >99%) and the e.e. was not decreased by heat treatment of the cell-free extract or the acetone-dried cells. The active fractions shown by two peaks on a DEAE-Toyopearl 650 M column gave preferentially (S)-ECHB (e.e.; >99%).
Saratani
Y
Y
Research Institute for Advanced Science and Technology, Osaka Prefecture University, Sakai, Japan.
Uheda
E
E
Yamamoto
H
H
Nishimura
A
A
Yoshizako
F
F
D000090:Acetoacetates / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D002087:Butyrates / Q000737:chemistry / Q000378:metabolism; D005658:Fungi / Q000378:metabolism*; D006999:Hypocreales / Q000378:metabolism; D007700:Kinetics; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000090:Acetoacetates; D002087:Butyrates; C121244:ethyl 4-chloro-3-hydroxybutanoate; C111982:ethyl 4-chloro-3-oxobutanoate