Stereoselective reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae.
A comparative study of two modifications of enzymic reduction of ethyl N-[2-[4-[(2-oxo-cyclohexyl)methyl]phenoxy]ethyl]carbamate (1), an insect juvenile hormone bioanalog, was performed using Saccharomyces cerevisiae in two bioreactors of different size, 250-ml shake-flask and 1-l fermenter. The two major products of this reduction were obtained in 45-49% (w/w) yields but with > 99% enantiomeric purity. Their absolute configurations were assigned as ethyl (1S,2S)-N-[2-[4-[(2-hydroxycyclohexyl)methyl]phenoxy]ethyl]carbamate (2a) and ethyl (1R,2S)-N-[2-[4-[(2-hydroxycyclohexyl)methyl]phenoxy]ethyl]carbamate (3a).
Zarevúcka
Marie
M
Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo námestí 2, CZ-16610 Prague 6, Czech Republic.
Sochůrková
Pavla
P
Wimmer
Zdenek
Z
Saman
David
D
D000438:Alcohols / Q000378:metabolism*; D019149:Bioreactors; D002219:Carbamates / Q000378:metabolism*; D003512:Cyclohexanones / Q000378:metabolism*; D010084:Oxidation-Reduction; D010865:Pilot Projects; D011786:Quality Control; D012441:Saccharomyces cerevisiae / Q000737:chemistry / Q000145:classification / Q000201:enzymology / Q000378:metabolism*; D013045:Species Specificity; D013237:Stereoisomerism
D000438:Alcohols; D002219:Carbamates; D003512:Cyclohexanones