Biosynthesis of synthons in two-liquid-phase media

Biotechnology and Bioengineering

Volumn 52, Issue 2, 1996, Pages 301-308

  Wubbolts, Marcel G ^a   Favre Bulle, Olivier ^b   Witholt, Bernard ^a  

^a ETH ZURICH   (Switzerland)

^b SANOFI   (France)

Author keywords

alkane hydroxylase; octanoic acid; styrene oxide; two liquid phase biocatalysis; xylene oxygenase

Indexed keywords

BACTERIA; BIOCONVERSION; CARBOXYLIC ACIDS; CATALYSIS; ENZYMES; OXIDATION; PARAFFINS; STYRENE;

ALIPHATIC HYDROCARBONS; ALKANEHYDROXYLASE; ESCHERICHIA COLI; OCTANOIC ACID; STYRENE OXIDE; SYNTHONS; TWO LIQUID PHASE BIOCATALYSIS; XYLENE OXYGENASE;

BIOSYNTHESIS;

OXYGENASE; UNCLASSIFIED DRUG;

BIOTRANSFORMATION; CELL DENSITY; CONFERENCE PAPER; ENZYME BINDING; PSEUDOMONAS; PSEUDOMONAS PUTIDA; STRAIN DIFFERENCE; SYNTHON;

EID: 10144232091     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19961020)52:2<301::AID-BIT10>3.0.CO;2-M     Document Type: Conference Paper

References (37)

1. Aono, R., Kobayashi, H., Joblin, K. N., Horikoshi, K. 1994. Effects of organic solvents on growth of Escherichia coli K-12. Biosci. Biotechnol. Biochem. 58: 2009-2014.
2. Baptist, J. N., Gholson, R. K., Coon, M. J. 1963. Hydrocarbon oxidation by a bacterial enzyme system. I. Products of octane oxidation. Biochim. Biophys. Acta 69: 40-47.
3. Benson, S., Shapiro, J. 1975. Induction of alkane hydroxylase proteins by unoxidized alkane in Pseudomonas putida. J. Bacteriol. 123: 759-760.
4. Boronin, A. M. 1991. Genetics of biodegradation. Acta Biotechnol. 11: 177-181.
5. Boyer, H. W., Roulland-Dussoix, D. 1969. A complementation analysis of the restriction and modification of DNA in Escherichia coli. J. Mol. Biol. 41: 459-472.
6. Burlage, R. S., Hooper, S. W., Sayler, G. S. 1989. The TOL (pWWO) catabolic plasmid. Appl. Environ. Microbiol. 55: 1323-1328.
7. de Smet, M.-J. 1983. A biotechnological approach to the synthesis of epoxides: Bioconversions of hydrocarbons by Pseudomonas oleovorans during growth in a multiphase system. Biotechnol. Bioeng. 25: 1161-1162.
8. de Smet, M. J., Kingma, J., Wynberg, H., Witholt, B. 1983. Pseudomonas oleovorans as a tool in bioconversions of hydrocarbons: Growth morphology and conversion characteristics in different two-phase systems. Enzyme Microb. Technol. 5: 352-360.
9. Eggink, G., Lageveen, R. G., Altenburg, B., Witholt, B. 1987. Controlled and functional expression of the Pseudomonas oleovorans alkane utilizing system in Pseudomonas putida and Escherichia coli. J. Biol. Chem. 262: 17712-17718.
10. Favre-Bulle, O. 1992. Escherichia coli as a potential hydrocarbon bioconversion organism. Ph.D. Dissertation, University of Groningen, The Netherlands.
11. Favre Bulle, O., Witholt, B. 1992. Biooxidation of n-octane by a recombinant Escherichia coli in a two-liquid-phase system: Effect of medium components on cell growth and alkane oxidation activity.
12. Favre Bulle, O., Schouten, T., Kingma, J., Witholt, B. 1991. Bioconversion of n-octane to octanoic acid by a recombinant Escherichia coli cultured in a two-liquid phase bioreactor. Bio/Technology 9: 367-371.
13. +) growing in a two-liquid-phase chemostat. Biotechnol. Bioeng. 41: 263-272.
14. Fieschko, J., Ritch, T. 1986. Production of human alpha consensus interferon in recombinant Escherichia coli. Chem. Eng. Commun. 45: 229-240.
15. Franklin, F. C. H., Lehrbach, P. R., Lurz, R., Rueckert, B., Bagdasarian, M., Timmis, K. N. 1983. Localization and functional analysis of transposon mutations in regulatory genes of the TOL catabolic pathway. J. Bacteriol. 154: 676-685.
16. Furuhashi, K. 1992. Biological routes to optically active epoxides, pp. 167-186. In: A. N. Collins, G. N. Sheldrake, and J. Crosby (eds.), Chirality in industry. Wiley, London.
17. Harayama, S., Kok, M., Neidle, E. L. 1992. Functional and evolutionary relationships among diverse oxygenases. Ann. Rev. Microbiol. 46: 565-601.
18. Harayama, S., Rekik, M., Wubbolts, M., Rose, K., Leppik, R. A., Timmis, K. N. 1989. Characterization of five genes in the upper-pathway operon of TOL plasmid pWWO from Pseudomonas putida and identification of the gene products. J. Bacteriol. 171:5048-5055.
19. Inoue, A., Horikoshi, K. 1991. Estimation of solvent tolerance of bacteria by the solvent parameter log P. J. Ferment. Bioeng. 71: 194-196.
20. Katopodis, A. G. 1982. Mechanistic studies on the epoxidation system of Pseudomonas oleovorans. Ph.D. Dissertation, University of Georgia.
21. Katsuki, T., Sharpless, K. B. 1980. The first practical method for asymmetric epoxidation. J. Am. Chem. Soc. 102: 5974-5976.
22. Kieslich, K. 1991. Biotransformations of industrial use. Acta Biotechnol. 11: 559-570.
23. Laane, C., Boeren, S., Vos, K., Vergeer, C. 1987. Rules for optimization of biocatalysis in organic solvents. Biotechnol. Bioeng. 30: 81-87.
24. Maniatis, T., Fritsch, E. H., Sambrook, J. 1982. Molecular cloning, a laboratory manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
25. Miller, J. H. 1972. Experiments in molecular genetics. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
26. Neidhardt, F. C. 1987. Chemical composition of E. coli B, pp. 3-7. In: F. C. Neidhardt, J. L. Ingraham, K. B. Low, B. Magasanik, M. Schaechter, and H. E. Umbarger (eds.), Escherichia coli and Samonella typhimurium: Cellular and molecular biology, vol. 2. American Society for Microbiology, Washington DC.
27. Nöthe, C., Hartmans, S. 1994. Formation and degradation of styrene oxide stereoisomers by different microorganisms. Biocatalysis 10: 219-225.
28. Ohta, H., Tetsukawa, H. J. 1978. Microbial epoxidation of long-chain terminal olefins. J. Chem. Soc. Chem. Commun. 742: 849-850.
29. Preusting, H., van Houten, R., Hoefs, A., van Langenberghe, E. K., Favre Bulle, O., Witholt, B. 1993. High cell density cultivation of Pseudomonas oleovorans: Growth and production of poly(3-hydroxy-alkanoates) in two-liquid phase batch and fed-batch systems. Biotechnol. Bioeng. 41: 550-556.
30. Riesenberg, D., Schulz, V., Knorre, W. A., Pohl, H.-D., Kortz, D., Sanders, E. A., A., R., Deckwer, W. D. 1991. High cell density cultivation of Escherichia coli at controlled specific growth rate. J. Biotechnol. 20: 17-28.
31. Shamel, R. E., Chow, J. 1988. Biotech's potential impact on the chemical industry. Bio/Technology 6: 681-682.
32. Shu, J., Shuler, M. L. 1991. Prediction of effects of amino acid supplementation on growth of E. coli B/r. Biotechnol. Bioeng. 37: 708-715.
33. Suzuki, M., Hayakawa, T., Shaw, J. P., Rekik, M., Harayama, S. 1991. Primary structure of xylene monooxygenase: Similarities to and differences from the alkane hydroxylation system. J. Bacteriol. 173: 1690-1695.
34. Wubbolts, M. G. 1994. Xylene and alkane mono-oxygenases from Pseudomonas putida. Ph.D. Dissertation, University of Groningen, Groningen, The Netherlands.
35. Wubbolts, M. G., Hoven, J., Melgert, B., Witholt, B. 1994a. Efficient production of optically active styrene epoxides in two-liquid phase cultures. Enz. Microb. Technol. 16: 887-894.
36. Wubbolts, M. G., Reuvekamp, P., Witholt, B. 1994b. TOL plasmid-specified xylene oxygenase is a wide substrate range monooxygenase capable of olefin epoxidation. Enz. Microb. Technol. 16: 608-615.
37. Zhang, W., Loebach, L. J., Wilson, R. S., Jacobson, N. E. 1990. Enantioselective epoxidation of unfunctionalized olefins catalyzed by (salen) manganese complexes. J. Am. Chem. Soc. 112: 2801-2803.