Microbial oxidation of cumene by octane-grown cells

Previously, we reported that eight glucose-grown microbial cultures out of 1229 screened oxidize the alkyl side-chain of 2-phenylpropane (cumene) stereospecifically. Now, we have adapted these cultures to grow on n-octane and found that their cumene oxidation activities increased more than 30 times. We also found an additional 11 cultures (ten bacteria, one actinomycete) that oxidized cumene when grown on octane but not on glucose. In general, octane-grown cells were more active in cumene oxidation than glucose-grown cells. Rhodococcus rhodochrous NRRL B-2153 showed the best conversion yield (2-phenyl-1-propanol plus 2-phenyl-1-propionic acid was 5.5%) at 25 degrees C, pH 8.0, 250 rpm, and 12 h of reaction. Structures of the reaction products were confirmed by gas chromatography (GC)/mass spectrometry and GC/infrared analyses. Products contained 84% ee (enantiomeric excess) of the R(-) isomer, as analyzed with a GC cyclodextrin chiral column. Strain B-2153 oxidized alkylbenzenes in the following order of reaction rate: ethylbenzene > amylbenzene > butylbenzene > cumene > propylbenzene > sec-butylbenzene. tert-Butylbenzene was not oxidized.