Microbial obtainment of (R)- and (S)-2-octanol was studied. Two strategies were developed: kinetic resolution of 2-octanol racemic mixture through selective oxidation and enantioselective reduction of 2-octanone. Two strains of acetic acid bacteria were found to preferentially oxidize (R)-2-octanol with moderate discrimination between the enantiomers. Various microorganisms belonging to different genera gave 2-octanone reduction with general preference for (S)-2-octanol formation. Lactobacillus fermentum ILC G18D, Acetobacter sp. CH MIM, Candida boidinii CBS 2428 and Pichia fermentans DPVPG 2770 afforded (S)-2-octanol with an enantiomeric excess (e.e.) greater than 97%. Reduction of shorter chain methyl ketones with Candida boidinii and Pichia fermentans showed that the ketone structure was extremely important to the transformation stereobias.
Microbial biotransformations to obtain (R)- and (S)-2-octanol / F. Molinari, C. Bertolini, F. Aragozzini. - In: ANNALI DI MICROBIOLOGIA ED ENZIMOLOGIA. - ISSN 0003-4649. - 47:1(1997), pp. 131-137.
Microbial biotransformations to obtain (R)- and (S)-2-octanol
F. MolinariPrimo
;
1997
Abstract
Microbial obtainment of (R)- and (S)-2-octanol was studied. Two strategies were developed: kinetic resolution of 2-octanol racemic mixture through selective oxidation and enantioselective reduction of 2-octanone. Two strains of acetic acid bacteria were found to preferentially oxidize (R)-2-octanol with moderate discrimination between the enantiomers. Various microorganisms belonging to different genera gave 2-octanone reduction with general preference for (S)-2-octanol formation. Lactobacillus fermentum ILC G18D, Acetobacter sp. CH MIM, Candida boidinii CBS 2428 and Pichia fermentans DPVPG 2770 afforded (S)-2-octanol with an enantiomeric excess (e.e.) greater than 97%. Reduction of shorter chain methyl ketones with Candida boidinii and Pichia fermentans showed that the ketone structure was extremely important to the transformation stereobias.Pubblicazioni consigliate
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