Reduction of carbon-carbon double bonds using Acetobacterium woodii: Determination of the optimum inducer structure

Farhad Foroughi, Paul Williams, Gill Stephens

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Various cinnamate derivatives were tested as inducers for reduction of C-C double bonds in Acetobacterium woodii. The double bond and a phenyl ring were essential for induction, since crotonate and hydrocaffeate were ineffective as inducers whereas cinnamate derivatives were effective. Induction was improved by ring hydroxylation, except in the 2-position, since caffeate and 3- and 4-hydroxy cinnamate were the most effective inducers. The carboxylate group of cinnamate could be replaced by ester (methylcinnamate) or aldehyde (cinnamaldehyde), but not by alcohol (cinnamyl alcohol) or methyl (trans-β-methylstyrene). Effective inducers were hydrogenated efficiently during growth, whereas ineffective inducers were not metabolised. Several inducers with intermediate effectiveness were hydrogenated in low yield with accompanying metabolism of other functional groups. Overall, caffeate (3,4-dihydroxycinnamate) was the best inducer. © 2006 Elsevier Inc. All rights reserved.
    Original languageEnglish
    Pages (from-to)1066-1071
    Number of pages5
    JournalEnzyme and Microbial Technology
    Volume39
    Issue number5
    DOIs
    Publication statusPublished - 4 Sep 2006

    Keywords

    • Acetobacterium woodii
    • Biocatalysis
    • Biocatalytic hydrogenation
    • C-C double bond reduction
    • Inducer structure

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