Bacterial Oxidation of 2-Tridecanone to 1-Undecanol

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Abstract
A study of the microbial utilization of long-chain methyl ketones was undertaken. In general, enrichment culture experiments revealed that soil microorganisms capable of utilizing these compounds as growth substrates are ubiquitous. Gram-negative, rod-shaped bacteria were the prominent organisms exhibiting this capability. In particular, a strain of Pseudomonas isolated from soil degraded 2-tridecanone into several products that were recovered from cell-free culture fluid. These products were identified by gas-liquid chromatography as 2-tridecanol, 1-undecanol, 1-decanol, and undecanoic acid. A large amount of the substrate was converted to 1 -undecanol. This compound was characterized further by classical methods of organic analysis. Unequivocal identification of 1 -undecanol has established that some unique mechanism that involves subterminal oxidation must exist to degrade 2-tridecanone. No such mechanism has been reported for the biological degradation of long-chain, aliphatic, methyl ketones. A pathway for utilization of 2-tridecanone was proposed that is consistent with, but not confirmed by, the data presented.