Carbon metabolism and product inhibition determine the epoxidation efficiency of solvent-tolerant Pseudomonas sp. strain VLB120ΔC

Biotechnology and Bioengineering

Volumn 98, Issue 6, 2007, Pages 1219-1229

  Park, Jin Byung ^a   Bühler, Bruno ^b   Panke, Sven ^c   Witholt, Bernard ^c   Schmid, Andreas ^b  

^a Ewha Womans University   (South Korea)

^b TU DORTMUND UNIVERSITY   (Germany)

^c ETH ZURICH   (Switzerland)

Author keywords

Biocatalysis; Carbon metabolism; Oxygenase; Pseudomonas; Solvent tolerance; Two liquid phase

Indexed keywords

BIOCATALYSTS; CARBON; ENZYME INHIBITION; METABOLISM; SOLVENTS; TOXIC MATERIALS;

BIOCATALYSIS; CARBON METABOLISM; OXYGENASE; PSEUDOMONAS; SOLVENT TOLERANCE; TWO-LIQUID PHASE;

BACTERIA;

PHENETHYL ALCOHOL; STYRENE OXIDE;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BIOCATALYST; BIOTRANSFORMATION; CARBON METABOLISM; CATABOLITE REPRESSION; CONTROLLED STUDY; ENZYME ACTIVITY; EPOXIDATION; ESCHERICHIA COLI; NONHUMAN; PSEUDOMONAS; STEADY STATE;

CARBON; DRUG TOLERANCE; EPOXY COMPOUNDS; GENETIC ENGINEERING; MUTATION; PSEUDOMONAS; SOLVENTS; STEREOISOMERISM;

ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS SP.;

EID: 34147104660     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.21496     Document Type: Article

References (51)

1. Axe DD, Bailey JE. 1995. Transport of lactate and acetate through the energized cytoplasmic membrane of Escherichia coli. Biotechnol Bioeng 47:8-19.
2. Besse P, Veschambre H. 1994. Chemical and biological synthesis of chiral epoxides. Tetrahedron 50:8885-8927.
3. Bühler B, Witholt B, Hauer B, Schmid A. 2002. Characterization and application of xylene monooxygenase for multistep biocatalysis. Appl Environ Microbiol 68:560-568.
4. Bühler B, Bollhalder I, Hauer B, Witholt B, Schmid A. 2003a. Chemical biotechnology for the specific oxyfunctionalization of hydrocarbons on a technical scale. Biotechnol Bioeng 82:833-842.
5. Bühler B, Bollhalder I, Hauer B, Witholt B, Schmid A. 2003b. Use of the two-liquid phase concept to exploit kinetically controlled multistep biocatalysis. Biotechnol Bioeng 81:683-694.
6. Bühler B, Straathof AJJ, Witholt B, Schmid A. 2006. Analysis of two-liquid-phase multistep biooxidation based on a process model: Indications for biological energy shortage. Org Proc Res Dev 10:628-643.
7. Collier DN, Hager PW, Phibbs PV. 1996. Catabolite repression control in the Pseudomonads. Res Microbiol 147:551-561.
8. Desomer J, Crespi M, Van Montagu M. 1991. Illegitimate integration of non-replicative vectors in the genome of Rhodococcus fascians upon elctrotransformation as an insertional mutagenesis system. Mol Microbiol 5:2115-2124.
9. Duetz WA, van Beilen JB, Witholt B. 2001. Using proteins in their natural environment: Potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis. Curr Opin Biotechnol 12:419-425.
10. Faber K, Patel R. 2000. Chemical biotechnology. A happy marriage between chemistry and biotechnology: Asymmetric synthesis via green chemistry. Curr Opin Biotechnol 11:517-519.
11. Han JH, Park MS, Bae JW, Lee EY, Yoon YJ, Lee SG, Park S. 2006. Production of (S)-styrene oxide using styrene oxide isomerase negative mutant of Pseudomonas putida SN1. Enzyme Microb Technol 39:1264-1269.
12. Heipieper HJ, Meinhardt F, Segura A. 2003. The cis-trans isomerase of unsaturated fatty acids in Pseudomonas and Vibrio: Biochemistry, molecular biology and physiological function of a unique stress adaptive mechanism. FEMS Microbiol Lett 229:1-7.
13. Hofstetter K, Lutz J, Lang I, Witholt B, Schmid A. 2004. Coupling of biocatalytic asymmetric epoxidation with NADH regeneration in organic-aqueous emulsions. Angew Chem Int Ed Engl 43:2163-2166.
14. Inoue A, Horikoshi K. 1989. A Pseudomonas thrives in high concentrations of toluene. Nature 338:264-266.
15. Isken S, de Bont JA. 1998. Bacteria tolerant to organic solvents. Extremophiles 2:229-238.
16. Jimenez JI, Minambres B, Garcia JL, Diaz E. 2002. Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440. Environ Microbiol 4:824-841.
17. Junker F, Ramos JL. 1999. Involvement of the cis/trans isomerase Cti in solvent resistance of Pseudomonas putida DOT-T1E. J Bacteriol 181:5693-5700.
18. Kantz A, Chin F, Nallamothu N, Nguyen T, Gassner GT. 2005. Mechanism of flavin transfer and oxygen activation by the two-component flavoenzyme styrene monooxygenase. Arch Biochem Biophys 442:102-116.
19. Kieboom J, Dennis JJ, de Bont JA, Zylstra GJ. 1998. Identification and molecular characterization of an efflux pump involved in Pseudomonas putida S12 solvent tolerance. J Biol Chem 273:85-91.
20. Leoni L, Rampioni G, Di Stefano V, Zennaro E, 2005. Dual role of response regulator StyR in styrene catabolism regulation. Appl Environ Microbiol 71:5411-5419.
21. Li Z, van Beilen JB, Duetz WA, Schmid A, de Raadt A, Griengl H, Witholt B. 2002. Oxidative biotransformations using oxygenases. Curr Opin Chem Biol 6:136-144.
22. Mooney A, Ward PG, O'Connor KE. 2006. Microbial degradation of styrene: Biochemistry, molecular genetics, and perspectives for biotechnological applications. Appl Microbiol Biotechnol 72:1-10.
23. Nelson KE, Weinel C, Paulsen IT, Dodson RJ, Hubert H, dos Santos VAPM, Fouts DE, Gill SR, Pop M, Holmes M, et al. 2002. Complete genome sequence and comparative analysis of the metabolically versatile Pseudomonas putida KT2440. Environ Microbiol 4:799-808.
24. Nöthe C, Hartmans S. 1994. Formation and degradation of styrene oxide stereoisomers by different microorganisms. Biocatalysis 10:219-225.
25. O'Connor K, Buckley CM, Hartmans S, Dobson AD. 1995. Possible regulatory role for nonaromatic carbon sources in styrene degradation by Pseudomonas putida CA-3. Appl Environ Microbiol 61:544-548.
26. O'Connor K, Duetz W, Wind B, Dobson ADW. 1996. The effect of nutrient limitation on styrene metabolism in Pseudomonas putida CA-3. Appl Environ Microbiol 62:3594-3599.
27. O'Connor KE, Dobson AD, Hartmans S. 1997. Indigo formation by microorganisms expressing styrene monooxygenase activity. Appl Environ Microbiol 63:4287-4291.
28. O'Leary ND, O'Connor KE, Duetz W, Dobson ADW. 2001. Transcriptional regulation of styrene degradation in Pseudomonas putida CA-3. Microbiology 147:973-979.
29. Otto K, Hofstetter K, Rothlisberger M, Witholt B, Schmid A. 2004. Biochemical characterization of StyAB from Pseudomonas sp. strain VLB 120 as a two-component flavin-diffusible monooxygenase. J Bacteriol 186:5292-5302.
30. Panke S. 1999. Production of (S)-styrene oxide with recombinant bacteria. Ph.D. thesis, Swiss Federal Institute of Technology, Zurich.
31. Panke S, Witholt B, Schmid A, Wubbolts MG. 1998. Towards a biocatalyst for (S)-styrene oxide production: Characterization of the styrene degradation pathway of Pseudomonas sp. strain V LB120. Appl Environ Microbiol 64:2032-2043.
32. Panke S, Wubbolts MG, Schmid A, Witholt B. 2000. Production of enantiopure styrene oxide by recombinant Escherichia coli synthesizing a two-component styrene monooxygenase. Biotechnol Bioeng 69:91-100.
33. Park JB. 2004. The productivity of biocatalytic epoxidation of styrene to (S)-styrene oxide. Ph.D. thesis, Swiss Federal Institute of Technology, Zurich.
34. Park JB, Bühler B, Habicher T, Hauer B, Panke S, Witholt B, Schmid A. 2006. The efficiency of recombinant Escherichia coli as biocatalyst for stereospecific epoxidation. Biotechnol Bioeng 95:501-512.
35. Prentki P, Krisch HM. 1984. In vitro insertional mutagenesis with a selectable DNA fragment. Gene 29:303-313.
36. Ramos JL, Duque E, Huertas MJ, Haidour A. 1995. Isolation and expansion of the catabolic potential of a Pseudomonas putida strain able to grow in the presence of high concentrations of aromatic hydrocarbons. J Bacteriol 177:3911-3916.
37. Ramos JL, Duque E, Gallegos MT, Godoy P, Ramos-Gonzalez MI, Rojas A, Teran W, Segura A. 2002. Mechanisms of solvent tolerance in Gram-negative bacteria. Annu Rev Microbiol 56:743-768.
38. Ramos-Gonzalez MI, Godoy P, Alaminos M, Ben-Bassat A, Ramos JL. 2001. Physiological characterization of Pseudomonas putida DOT-T1E tolerance to p-hydroxybenzoate. Appl Environ Microbiol 67:4338-4341.
39. Ramos-Gonzalez MI, Ben-Bassat A, Campos MJ, Ramos JL. 2003. Genetic engineering of a highly solvent-tolerant Pseudomonas putida strain for biotransformation of toluene to p-hydroxybenzoate. Appl Environ Microbiol 69:5120-5127.
40. Rothen SA, Sauer M, Sonnleitner B, Witholt B. 1998. Biotransformation of octane by E. coli HB101[pGEc47] on defined medium: Octanoate production and product inhibition. Biotechnol Bioeng 58:356-365.
41. Sambrook J, Fritsch EF, Maniatis T. 1989. Molecular cloning: A laboratory manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
42. Santos PM, Blatny JM, Di Bartolo I, Valla S, Zennaro E. 2000. Physiological analysis of the expression of the styrene degradation gene cluster in Pseudomonas fluorescens ST. Appl Environ Microbiol 66:1305-1310.
43. Schmid A, Sonnleitner B, Witholt B. 1998. Medium chain length alkane solvent-cell transfer rates in two-liquid phase, Pseudomonas oleovorans cultures. Biotechnol Bioeng 60:10-23.
44. Schweizer HP, Hoang TT. 1995. An improved system for gene replacement and xylE fusion analysis in Pseudomonas aeruginosa. Gene 158:15-22.
45. Segura A, Rojas A, Hurtado A, Huertas MJ, Ramos JL. 2003. Comparative genomic analysis of solvent extrusion pumps in Pseudomonas strains exhibiting different degrees of solvent tolerance. Extremophiles 7:371-376.
46. Simon R, Priefer U, Pühler A. 1983. A broad host range mobilization system for in vivo genetic engineering: Transposon mutagenesis in Gram-negative bacteria. Bio-Technology 1:784-791.
47. + recombinants. J Bacteriol 181:1610-1616.
48. Staijen IE, van Beilen JB, Witholt B. 2000. Expression, stability and performance of the three-component alkane mono-oxygenase of Pseudomonas oleovorans in Escherichia coli. Eur J Biochem 267:1957-1965.
49. Weber FJ, Ooijkaas LP, Schemen RMW, Hartmans S, de Bont JAM. 1993. Adaptation of Pseudomonas putida S12 to high concentrations of styrene and other organic solvents. Appl Environ Microbiol 59:3502-3504.
50. Wery J, Mendes da Silva DI, de Bont JAM. 2000. A genetically modified solvent-tolerant bacterium for optimized production of a toxic fine chemical. Appl Microbiol Biotechnol 54:180-185.
51. Wubbolts MG, FavreBulle O, Witholt B. 1996. Biosynthesis of synthons in two-liquid-phase media. Biotechnol Bioeng 52:301-308.