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Biocatalysis pp 147-159 | Cite as

Bacterial Biotransformation of Isopreneand Related Dienes

  • Derek R. Boyd
  • David Clarke
  • Marcel C. Cleij
  • John T. G. Hamilton
  • Marcel N. Sheldrake

Abstract

The bacterium Pseudomonas putida ML 2 was used in the oxidative biodegradation of the acyclic dienes isoprene, trans-piperylene, cis-piperylene, and 1,3-butadiene. Regioselective dioxygenase-catalyzed dihydroxylation of alkenes yielded vicinal diols in the preferred sequence monosubstituted > cis-disubstituted > gem-disubstituted > trans-disubstituted. The isolated diol metabolites had an excess of the R configuration (9-97% ee), and further diol oxidation was controlled by addition of propylene glycol as an inhibitor. Stereoselectivity using the ML2 strain resulted from both enzymatic asymmetric alkene dihydroxylation and kinetic resolution of diols. Enantioselective oxidation of the allylic secondary alcohol group of R configuration yielded the corresponding unsaturated ketoalcohol; the residual diol was recovered with a large excess (> 93% ee) of the S configuration. In addition to the enzymatic diene oxidation steps yielding unsaturated diols and ketoalcohols, evidence was also found of enzymatic alkene hydrogenation to yield saturated ketoalcohols and diols.

Keywords

Propylene Glycol Chiral Stationary Phase Kinetic Resolution Toluene Dioxygenase Ketone Reduction 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer-Verlag Vienna 2000

Authors and Affiliations

  • Derek R. Boyd
    • 1
  • David Clarke
    • 1
  • Marcel C. Cleij
    • 1
  • John T. G. Hamilton
    • 2
  • Marcel N. Sheldrake
    • 1
  1. 1.School of Chemistry and QUESTOR CentreThe Queen's University of BelfastUK
  2. 2.Food Science DivisionDepartment of Agriculture for Northern IrelandUK

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