Oxidative degradation of methyl ketones. II. Chemical pathway for degradation of 2-tridecanone by Pseudomonas multivorans and Pseudomonas aeruginosa

Abstract

A new intermediate was identified in the 2-tridecanone pathway of Pseudomonas multivorans, formerly designated pseudomonad 4G-9. This intermediate, undecyl acetate, was isolated directly from growing cultures of the organism; the structure of the intermediate was determined by infrared spectroscopy and by gas-liquid chromatographic identification of its hydrolytic products. An amended pathway is presented that accounts for the conversion of 2-tridecanone to provide carbon and energy for growth. It was shown that all early intermediates in the pathway arise biologically and sequentially from their precursors. Studies with P. aeruginosa showed that this organism also degrades 2-tridecanone by the pathway characteristic of P. multivorans. Biochemical mechanisms of the pathway are discussed. Discovery of undecyl acetate confirms our earlier contention that the primary attack on methyl ketones by bacteria can be by subterminal oxidation.