Microbial reduction of cyclohexanones

A Brazilian strain of the bacteria Serratia rubidaea CCT 5742 quantitatively reduced 4-tert-butylcyclohexanone and 4-methylcyclohexanone to the less thermodynamically stable diastereoisomeric alcohols cis-4-tert-butylcyclohexanol and cis-4-methylcyclohexanol with a diastereoisomeric excesses (de) of...

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Published inJournal of molecular catalysis. B, Enzymatic Vol. 11; no. 4-6; pp. 233 - 236
Main Authors De Conti, Roseli Maria, Porto, André L.M., Augusto, J., Rodrigues, R., Moran, Paulo J.S., Manfio, Gilson P., Marsaioli, Anita J.
Format Journal Article Conference Proceeding
LanguageEnglish
Published Amsterdam Elsevier B.V 22.01.2001
Elsevier Science
Subjects
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Cyclohexanones
Diastereo- and enantioselective reductions
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Serratia rubidaea
Diastereo- and enantioselective reductions
Cyclohexanones
Serratia rubidaea
Chemical reduction
Enantioselectivity
Biotransformation
Bacteria
Diastereoselectivity
Enterobacteriaceae
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Summary:A Brazilian strain of the bacteria Serratia rubidaea CCT 5742 quantitatively reduced 4-tert-butylcyclohexanone and 4-methylcyclohexanone to the less thermodynamically stable diastereoisomeric alcohols cis-4-tert-butylcyclohexanol and cis-4-methylcyclohexanol with a diastereoisomeric excesses (de) of 96% and 44%, respectively. 2-Methylcyclohexanone was also totally reduced to the corresponding alcohols affording the trans-(+)-(1S, 2S)-2-methylcyclohexanol with 78% of de and an enantiomeric excess (ee) of 80%. The cis-(+)-(1S, 2R)-2-methylcyclohexanol was obtained in 98% ee.
ISSN:1381-1177
1873-3158
DOI:10.1016/S1381-1177(00)00087-4