Intermediates from the microbial oxidation of aliphatic hydrocarbons

Oxidation of aliphatic saturated and unsaturated hydrocarbons by bacteria, yeasts, and fungi leads to the production of a variety of intermediates, e.g., mono‐ and dicarboxylic acids, primary alcohols, isomeric alcohols and their corresponding ketones, diols, epoxides, and hydroxy acids. Further degradation of isomeric ketones in two species ofPseudomonas occurs by a flavoprotein monooxygenase leading to the formation of ester intermediates. In the case of 2‐tridecanone→undecyl acetate, the esterase active on the acetate ester also has been characterized. Oxidation of pristane gives rise to several branched chain intermediates of varying carbon length. Products from other branched chain hydrocarbons are also presented. Oxidation of hydrocarbons that are not growth substrates but are nonetheless oxidized by microorganisms is reviewed. The examples presented reiterate the fact that microorganisms are a metabolically diverse group capable of altering an incredibly wide array of organic compounds of which aliphatic and alicyclic hydrocarbons as a class represent but one example.