Enantioselective reduction of 3,4-methylene-dioxyphenylacetone using Candida famata and Zygosaccharomyces rouxii.
In an effort to prepare 3,4-methylene-dioxyphenyl-(S)-isopropanol from 3,4-methylene-dioxyphenylacetone, an initial screen of microbes indicated that Candida famata could catalyze this reaction efficiently at low substrate concentration. A dilute, large-scale process was developed to provide experimental material for the chemical synthesis to be explored. However, the productivity number of this process [0.134 g product (g wet weight cells)-1 day-1 was too low to be practical. C. famata was also extremely sensitive to concentrations of both the ketone and the alcohol greater than 2 g/l. A more extensive screen of yeast and fungi revealed that Zygosaccharomyces rouxii was more tolerant to higher substrate concentrations and had a higher productivity number [0.8 g (g wet weight cells)-1 day-1]. These characteristics suggested that Z. rouxii could be used in a large-scale process at high substrate concentrations.
Zmijewski
M J
MJ
Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, USA. zmijew@lilly.com
Vicenzi
J
J
Landen
B E
BE
Muth
W
W
Marler
P
P
Anderson
B
B
D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D001709:Biotechnology; D002175:Candida / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism; D007700:Kinetics; D010084:Oxidation-Reduction; D004718:Saccharomycetales / Q000378:metabolism*; D013237:Stereoisomerism; D015003:Yeasts / Q000378:metabolism
C105881:3,4-methylene-dioxyphenylacetone; D000096:Acetone