Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by fungi.

Bioscience, biotechnology, and biochemistry (2001-08-23)
Y Saratani, E Uheda, H Yamamoto, A Nishimura, F Yoshizako
ABSTRACT

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%).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl 4-chloroacetoacetate, 95%
Sigma-Aldrich
Ethyl 4-chloroacetoacetate, Arxada quality, ≥97.0% (GC)