Abstract
The preponderant pathway of octene-1 degradation by octane- and octene-1-grownPseudomonas aeruginosa cells (strain 473) starts with oxidation of the methyl group.
In addition, with both types of cells minor reactions occur that involve the double bond. The formation of a 1,2-epoxide was reported earlier. In addition, the identification of the saturated C8 fatty acid is a strong indication that the terminal methylene group is partially converted into an aldehydic group. The aldehyde seems to be formed beside the epoxide and the latter is not an intermediate. Enzymatic dihydroxylation of the double bond, if at all occurring, is masked by non-enzymatic hydrolysis of the epoxide.
The formation of a saturated methyl ketone could not be detected. Nor is the olefinic group converted into a primary or secondary alcohol group under conditions which result in accumulation of octanol-1 from octane and of 7-octenol-1 from octene-1.
The absence of a saturated alcohol among the intermediates in octene-1 degradation excludes hydration of the double bond as well as other mechanisms leading to saturated alcohols.
Accumulation of C8 fatty acids was effected by inhibition of β-oxidation with acrylate, whereas addition of a competing alcohol substrate (octanediol-1,8) yielded detectable amounts of the alcoholic intermediates.
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Huybregtse, R., van der Linden, A.C. The oxidation of α-olefins by aPseudomonas reactions involving the double bond. Antonie van Leeuwenhoek 30, 185–196 (1964). https://doi.org/10.1007/BF02046725
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DOI: https://doi.org/10.1007/BF02046725