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.
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References
Atkinson R, Arey J (1998) Acc Chem Res 31: 574
Cleveland CC, Yavitt JB (1998) Appl Environ Microbiol 64: 172
Konig G, Brunda M, Puxbaum H, Hewitt CN, Duckham SC, RudolfJ(1995) JAtmos Environ 29: 861
Becker KH, Barnes I, Ruppert L (1994) Physico-Chemical Behaviour of Atmospheric Pollutants 1: 54
Peeters A, Ectors A, Boullart W (1994) Physico-Chemical Behaviour of Atmospheric Pollutants 1: 61
Madronich S, Calvert JG (1990) J Geophys Res 95: 5697
Bleasdale C, Small RD, Watson WP, Wilson J, Golding BT (1996) Toxicology 113: 290
Wistuba D, Weigand K, Peter H (1994) Chem Res Toxicol 7: 336
Longo V, Citti L, Gervasi PG (1985) Toxicology Letters 29: 33
Gervasi PG (1985) Mutat Res 156: 77
Allen CCR, Boyd DR, Dalton H, Sharma ND, Brannigan I, Kerley NA, Sheldrake GN, Taylor ST (1995) J Chem Soc Chem Commun 117
Allen CCR, Boyd DR, Hempenstall F, Larkin MJ, Sharma ND (1999) Appl and Environ Microbiol 65: 1335
Boyd DR, Sharma ND, Agarwal RA, Resnick SM, Schocken MJ, Gibson DT, Sayer JM, Yagi H, Jerina DM (1997) J Chem Soc Perkin Trans 1, 1715
Boyd DR, Sharma ND, Evans TA, Groocock MG, Malone JF, Stevenson PJ, Dalton H (1997) J Chem Soc Perkin Trans 1, 1879
Bowers NI, Boyd DR, Sharma ND, Kennedy MA, Sheldrake GN, Dalton H (1998) Tetrahedron Asymm 9: 1831
Boyd DR, Sharma ND, Haughey SA, Kennedy MA, McMurray BT, Sheldrake GN, Allen CCR, Dalton H, Sproule K (1998) J Chem Soc Perkin Trans 1, 1929
Lange CC, Wackett LP (1997) J Bacteriology 179: 3858
Kolb HC, VanNiewenhze MS, Sharpless KB (1994) Chem Rev 94: 2483
Wang ZM, Kakiuchi K, Sharpless KB (1995) J Org Chem 59: 6897
Allen CCR, Boyd DR, Dalton H, Sharma ND, Walker CE (in preparation)
Fong KPY, Goh CBH, Tan, H-M (1996) J Bacteriol 178: 5592
Allen, CCR, Boyd DR, Dalton H, Sharma ND, Brannigan I, Kerley NA, Sheldrake GN, Taylor SC (1994) Â J Chem Soc Chem 117
van Hylckama Vlieg JE, Leemhuis H, Spelberg JH, Janssen DB (2000) J Bacteriol 182: 1956
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Boyd, D.R., Clarke, D., Cleij, M.C., Hamilton, J.T.G., Sheldrake, M.N. (2000). Bacterial Biotransformation of Isopreneand Related Dienes. In: Griengl, H. (eds) Biocatalysis. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6310-8_12
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DOI: https://doi.org/10.1007/978-3-7091-6310-8_12
Publisher Name: Springer, Vienna
Print ISBN: 978-3-211-83527-2
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