Oxidation of Alkyl-substituted Cyclic Hydrocarbons by a Nocardia during Growth on n -Alkanes

Abstract

Nocardia 107-332, a soil isolate, oxidizes short-chain alkyl-substituted cyclic hydrocarbons to cyclic acids while growing on n -alkanes. Cyclic acids are produced also from relatively long-chain alkyl-substituted cyclics such as n -nonylbenzene or n -dodecylbenzene which alone support growth in a mineral-salts medium. ω-Oxidation of the alkyl substituents is followed by β-oxidation. It is of particular interest that cyclic acids such as cyclohexaneacetic and phenylacetic with C 2 residual carboxylic acid substituents are resistant to further oxidation by the nocardia but cyclic acids with C 1 or C 3 substituents are readily oxidized and utilized for growth. The specificity of microbial oxidations is demonstrated by the conversion of p -isopropyltoluene ( p -cymene) to p -isopropylbenzoic acid in n -alkane, growth-supported nocardia cultures.