Bacterial Biotransformation of Isopreneand Related Dienes
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.
KeywordsPropylene Glycol Chiral Stationary Phase Kinetic Resolution Toluene Dioxygenase Ketone Reduction
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- 2.Cleveland CC, Yavitt JB (1998) Appl Environ Microbiol 64: 172Google Scholar
- 3.Konig G, Brunda M, Puxbaum H, Hewitt CN, Duckham SC, RudolfJ(1995) JAtmos Environ 29: 861Google Scholar
- 4.Becker KH, Barnes I, Ruppert L (1994) Physico-Chemical Behaviour of Atmospheric Pollutants 1: 54Google Scholar
- 5.Peeters A, Ectors A, Boullart W (1994) Physico-Chemical Behaviour of Atmospheric Pollutants 1: 61Google Scholar
- 11.Allen CCR, Boyd DR, Dalton H, Sharma ND, Brannigan I, Kerley NA, Sheldrake GN, Taylor ST (1995) J Chem Soc Chem Commun 117Google Scholar
- 12.Allen CCR, Boyd DR, Hempenstall F, Larkin MJ, Sharma ND (1999) Appl and Environ Microbiol 65: 1335Google Scholar
- 17.Lange CC, Wackett LP (1997) J Bacteriology 179: 3858Google Scholar
- 19.Wang ZM, Kakiuchi K, Sharpless KB (1995) J Org Chem 59: 6897Google Scholar
- 20.Allen CCR, Boyd DR, Dalton H, Sharma ND, Walker CE (in preparation)Google Scholar
- 21.Fong KPY, Goh CBH, Tan, H-M (1996) J Bacteriol 178: 5592Google Scholar
- 22.Allen, CCR, Boyd DR, Dalton H, Sharma ND, Brannigan I, Kerley NA, Sheldrake GN, Taylor SC (1994) J Chem Soc Chem 117Google Scholar