Bacterial Biotransformation of Isoprene and Related Dienes |
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Authors: | Derek R. Boyd David Clarke Marcel C. Cleij John T. G Hamilton Gary N. Sheldrake |
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Affiliation: | (1) School of Chemistry and QUESTOR Centre, The Queen’s University of Belfast, Belfast BT9 5AG, UK, GB;(2) Food Science Division, Department of Agriculture for Northern Ireland, Belfast BT9 5PX, UK, IE |
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Abstract: | Summary. 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. Received December 20, 1999. Accepted (revised) February 7, 2000 |
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Keywords: | . Asymmetric dihydroxylation Chiral resolution Dioxygenases Enzymes Isoprene. |
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