Stereoselective Reduction of Ethyl 4-chloro-3-oxobutanoate by Fungi

Purification and Properties of a Carbonyl Reductase Involved in Stereoselective Reduction of Ethyl 4-Chloro-3-oxobutanoate fromCylindrocarpon sclerotigenumIFO 31855

“…7,14) In our previous paper, 6) we reported that whole cells of Cylindrocarpon sclerotigenum IFO 31855 stereoselectively reduced ECAA to (S )-ECHB with a À99z enantiomer excess (e.e.) and that their cell-free extract also converted ECAA to (S )-ECHB in the presence of NADPH (e.e.…”

“…2) Many studies have been reported on the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate (ECAA) to chiral alcohols using microorganisms. 1,[3][4][5][6][7][8] The several kinds of enzymes capable of reducing ECAA were isolated from yeasts; baker's yeast, 9,10) Sporobolomyces salmonicolor, 11) Candida magnoliae, 12) and Kluyveromyces lactis, 13) and characterized in detail.…”

“…6) The enzyme was puriˆed by four sequential column chromatographies at 0-49 C as follows. The standard buŠer, 50 mM potassium phosphate buŠer (KPB, pH 7.0) containing 20z glycerol and 0.5 mM DTT, was generally used throughout the enzyme puriˆcation.…”

Biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxy-butanoate in an aqueous-organic solvent biphasic system using Aureobasidium pullulans CGMCC 1244

“…It is known that a promiseful method for the stereoselective reduction of COBE is a biochemical approach involving microorganisms and enzymes, which have played a major role in the practical synthesis of the optically active CHBE. Various kinds of microorganisms have been employed to catalyze the asymmetric reduction of COBE to (S)-or (R)-CHBE in a whole-cells process [2][3][4][5][6]. Many COBE-reducing enzymes from Saccharomyces cerevisiae [7], Sporobolomyces salmonicolor [8][9][10], Candida magnoliae [11][12][13], Candida macedoniensis [14], Candida parapsilosis [15] and Kluyveromyces lactis [16] have been purified and characterized in detail.…”

Purification and cDNA Cloning of NADPH-Dependent Aldoketoreductase, Involved in Asymmetric Reduction of Methyl 4-Bromo-3-Oxobutyrate, from Penicillium citrinum IFO4631

“…␤-Hydroxyesters are useful for key pharmaceutical intermediates: L-carnitine from the (R)-enantiomer (19) and 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor from the (S)-enantiomer (13). Until now, some kinds of yeasts, fungi, and bacteria (1,3,13,14,15,17,18,19) have been found to catalyze the asymmetric reduction of ethyl 4-chloro-3-oxobutyrate to ethyl (S)-or (R)-4-chloro-3-hydroxybutyrate. However, there has been little information about the enzyme which could reduce methyl 4-bromo-3-oxobutyrate (BAM) to methyl (S)-4-bromo-3-hydroxybutyrate [(S)-BHBM].…”