Dioxygenase- and monooxygenase-catalysed synthesis of cis-dihydrodiols, catechols, epoxides and other oxygenated products

Biotechnology Letters

Volumn 30, Issue 11, 2008, Pages 1879-1891

  Nolan, Louise C ^a   O'Connor, Kevin E ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Biocatalysis; Dioxygenase; Directed evolution; Monooxygenase; Oxidase

Indexed keywords

AROMATIC COMPOUNDS; ARSENIC COMPOUNDS; BIOCHEMICAL ENGINEERING; BIODEGRADATION; CATALYSTS; CHLORINE COMPOUNDS; COMPLEXATION; GENETIC ENGINEERING; OXYGENATION; PROTEINS; TECHNOLOGY;

BIOCATALYSIS; DIOXYGENASE; DIRECTED EVOLUTION; MICROBIAL SOURCES; MONOOXYGENASE; OXIDASE; OXIDASE ENZYMES; OXIDOREDUCTASES; OXYGENATED PRODUCTS; PROTEIN ENGINEERING; RECOMBINANT ENZYMES; SELECTIVE OXYGENATION;

ENZYMES;

CATECHOL DERIVATIVE; DIOXYGENASE; EPOXIDE; MIXED FUNCTION OXIDASE; NAPHTHALENE DERIVATIVE;

CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; REVIEW;

CATALYSIS; CATECHOLS; DIOXYGENASES; EPOXY COMPOUNDS; MIXED FUNCTION OXYGENASES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NAPHTHALENES;

EID: 52449098459     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-008-9791-5     Document Type: Review

References (69)

1. SK Ahuja GM Ferreira AR Moreira 2004 Utilisation of enzymes for environmental applications Crit Rev Biotechnol 24 125 153
2. N Allouche M Damak R Ellouz S Sayadi 2004 Use of whole cells of Pseudomonas aeruginosa for synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol Appl Environ Microbiol 70 2105 2109
3. A Archelas R Furstoss 1997 Synthesis of enantiopure epoxides through biocatalytic approaches Annu Rev Microbiol 51 491 525
4. R Azerad 2001 Editorial overview: better enzyme for green chemistry Curr Opin Biotechnol 12 533 534
5. V Berberian CCR Allen ND Sharma DR Boyd C Hardacre 2007 A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method Adv Synth Catal 349 727 739
6. S Bernasconi F Orsini G Sello A Colmegna E Galli G Bestetti 2000 Bioconversion of substituted styrenes to the corresponding enantiomerically pure epoxides by a recombinant Escherichia coli strain Tetrahedron Lett 41 9157 9161
7. DR Boyd TDH Bugg 2006 Arene cis-dihydrodiol formation: from biology to application Org Biomol Chem 4 181 192
8. Boyd DR, Sharma ND, Belhocine T, Malone JF, McGregor S, Allen CCR (2006a) Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide derivatives: a new approach to the synthesis of enantiopure tetraoxygenated bioproducts from arenes. Chem Commun 47:4934-4936
9. DR Boyd ND Sharma NI Bowers H Dalton MD Garrett JS Harrison GN Sheldrake 2006 Dioxygenase-catalysed oxidation of disubstituted benzene substrates: benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect Org Biomol Chem 4 3343 3349
10. DR Boyd ND Sharma GP Coen PJ Gray JF Malone J Gawronski 2007 Enzyme-catalysed synthesis and absolute configuration assignments of cis-dihydrodiol metabolites from 1, 4-disubstituted benzenes Chemistry 13 5804 5811
11. SJ Brooks EM Doyle C Hewage JPG Malthouse W Duetz KE O'Connor 2004 Biotransformation of halophenols using crude cell extracts of Pseudomonas putida F6 Appl Microbiol Biotechnol 64 486 492
12. SJ Brooks EM Doyle KE O'Connor 2005 Tyrosol to hydroxytyrosol biotransformation by immobilised cells extracts of Pseudomonas putida F6 Enzyme Microb Technol 39 191 196
13. Bugg T (1997) An introduction to enzyme and coenzyme chemistry, 1st edn. Blackwell Science, Oxford
14. VP Bui TV Hansen Y Stenstrøm T Hudlicky 2000 Direct biocatalytic synthesis of functionalized catechols: a green alternative to traditional methods with high effective mass yield Green Chem 2 263 265
15. SG Burton 2003 Oxidising enzymes as biocatalysts Trends Biotechnol 21 543 549
16. KA Canada S Iwashita H Shim TK Wood 2002 Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation J Bacteriol 184 344 349
17. H Claus H Decker 2006 Bacterial tyrosinase Syst Appl Microbiol 29 3 14
18. P Di Gennaro P Conforti M Lasagni G Bestetti S Bernasconi F Orsini G Sello 2005 Dioxygenation of naphthalene by Pseudomonas fluorescens N3 dioxygenase: optimization of the process parameters Biotechnol Bioeng 93 511 518
19. WA Duetz JB van Beilen B Witholt 2001 Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis Curr Opin Biotechnol 12 419 425
20. JC Espín C Soler-Rivas E Cantos FA Tomás-Barberán HJ Wichers 2001 Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst J Agric Food Chem 49 1187 1193
21. Faber K (2004) Biotransformations in organic chemistry, 5th edn. Springer, Berlin
22. A Fishman Y Tao WE Bentley TK Wood 2004 Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene Biotechnol Bioeng 87 779 790
23. A Fishman Y Tao TK Wood 2004 Physiological relevance of successive hydroxylations of toluene by toluene para-monooxygenase of Ralstonia pickettii PK01 Biocat Biotrans 22 283 289
24. A Fishman Y Tao L Rui TK Wood 2005 Controlling the regiospecific oxidation of aromatics via active site engineering of toluene para-monooxygenase of Ralstonia pickettii PK01 J Biol Chem 280 506 514
25. S Halaouli M Asther J-C Sigoillot M Hamdi A Lomascolo 2006 Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications J Appl Microbiol 100 219 232
26. EG Hibbert PA Dalby 2005 Directed evolution strategies for improved enzymatic performance Microbial Cell Fact 4 29
27. EG Hibbert F Baganz HC Hailes JM Ward GJ Lye JM Woodley PA Dalby 2005 Directed evolution of biocatalytic processes Biomol Eng 22 11 19
28. GW Huisman D Gray 2002 Towards novel processes for the fine-chemical and pharmaceutical industries Curr Opin Biotechnol 13 352 358
29. S Husain 2008 Literature overview: microbial metabolism of high molecular weight polycyclic aromatic hydrocarbons Remed J 18 131 161
30. H Joo Z Lin FH Arnold 1999 Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation Nature 399 670 673
31. B Lavallee P Lessard P Vanrolleghem 2005 Review of procaryote metabolism in view of modeling microbial adaption from fast growth to starvation conditions J Environ Eng Sci 4 517 532
32. K Lee 2006 p-Hydroxylation reactions catalyzed by naphthalene dioxygenase FEMS Microbial Lett 255 316 320
33. EY Lee ML Shuler 2007 Molecular engineering of epoxide hydrolase and its application to asymmetric and enantioconvergent hydrolysis Biotechnol Bioeng 98 318 327
34. Z Li JB van-Beilen WA Duetz A Schmid AD Raadt H Griengl B Witholt 2002 Oxidative biotransformations using oxygenases Curr Opin Chem Biol 6 136 144
35. SW May MS Steltenkamp RD Schwartz CJ McCoy 1976 Stereoselective formation of diepoxides by an enzyme system of Pseudomonas oleovorans J Am Chem Soc 98 7856 7858
36. K McClay BG Fox RJ Steffan 2000 Toluene monooxygenase-catalyzed epoxidation of alkenes Appl Environ Microbiol 66 1877 1882
37. FM Menger 1993 Enzyme reactivity from an organic perspective Acc Chem Res 26 206 212
38. A Mooney PG Ward KE O'Connor 2006 Microbial degradation of styrene: biochemistry, molecular genetics, and perspectives for biotechnological applications Appl Microbiol Biotechnol 72 1 10
39. R Natarajan R Azerad B Badet E Copin 2005 Microbial cleavage of CF bond J Fluor Chem 126 424 435
40. T Nishio A Patel Y Wang PCK Lau 2001 Biotransformations catalyzed by cloned p-cymene monooxygenase from Pseudomonas putida F1 Appl Microbiol Biotechnol 55 321 325
41. LC Nolan KE O'Connor 2007 Use of Pseudomonas mendocina, or recombinant Escherichia coli cells expressing toluene-4-monooxygenase, and a cell-free tyrosinase for the synthesis of 4-fluorocatechol from fluorobenzene Biotechnol Lett 29 1045 1050
42. C Nöthe S Hartmans 1994 Formation and degradation of styrene oxide stereoisomers by different microorganisms Biocatalysis 10 219 225
43. ND O'Leary KE O'Connor ADW Dobson 2002 Biochemistry, genetics and physiology of microbial styrene degradation FEMS Microbiol Rev 26 403 417
44. K Otto K Hofstetter M Röthlisberger B Witholt A Schmid 2004 Biochemical characterization of styAB from Pseudomonas sp. strain VLB120 as a two-component flavin-diffusible monooxygenase J Bacteriol 186 5292 5302
45. S Panke V de Lorenzo A Kaiser B Witholt MG Wubbolts 1999 Engineering of a stable whole-cell biocatalyst capable of (S)-styrene oxide formation for continuous two-liquid-phase applications Appl Environ Microbiol 65 5619 5623
46. S Panke MG Wubbolts A Schmid B Witholt 2000 Production of enantiopure styrene oxide by recombinant Escherichia coli synthesizing a two-component styrene monooxygenase Biotechnol Bioeng 69 91 100
47. S Panke M Held MG Wubbolts B Witholt A Schmid 2002 Pilot-scale production of (S)-styrene oxide from styrene by recombinant Escherichia coli synthesizing styrene monooxygenase Biotechnol Bioeng 80 33 41
48. RE Parales NC Bruce A Schmid LP Wackett 2002 Biodegradation, biotransformation and biocatalysis (B3) Appl Environ Microbiol 68 4699 4709
49. J-B Park B Bühler T Habicher B Hauer S Panke B Witholt A Schmid 2006 The efficiency of recombinant Escherichia coli as biocatalyst for stereospecific epoxidation Biotechnol Bioeng 95 501 512
50. Patel RN (2007) Biocatalysis in the pharmaceutical and biotechnology industries, 1st edn. CRC Press, Boca Raton
51. P Pialis BA Saville 1998 Production of l-DOPA from tyrosinase immobilized on nylon 6, 6: enzyme stability and scaleup Enzyme Microbiol Technol 22 261 268
52. L Rui YM Kwon A Fishman KF Reardon TK Wood 2004 Saturation Mutagenesis of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chloroform degradation Appl Environ Microbiol 70 3246 3252
53. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001a) Industrial biocatalysis today and tomorrow. Nature 409:258-268
54. A Schmid K Hofstetter H-J Feiten F Hollmann B Witholt 2001 Integrated biocatalytic synthesis on gram scale: the highly enantioselective preparation of chiral oxiranes with styrene monooxygenase Adv Synth Catal 343 732 737
55. S-Y Seo Sharma Vk N Sharma 2003 Mushroom tyrosinase: recent prospects J Agric Food Chem 51 2837 2853
56. AJJ Straathof S Panke A Schmid 2002 The production of fine chemicals by biotransformations Chem Biotechnol 13 548 556
57. Y Tao A Fishman WE Bentley TK Wood 2004 Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone and methylhydroquinone J Bacteriol 186 4705 4713
58. Y Tao A Fishman WE Bentley TK Wood 2004 Oxidation of benzene to phenol, catechol, and 1, 2, 3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1 Appl Environ Microbiol 70 3814 3820
59. Y Tao WE Bentley TK Wood 2005 Phenol and 2-naphthol production by toluene 4-monooxygenases using an aqueous/dioctyl phthalate system Appl Microbiol Biotechnol 68 614 621
60. Y Tao WE Bentley TK Wood 2005 Regiospecific oxidation of naphthalene and fluorene by toluene monooxygenases and engineered toluene 4-monooxygenases of Pseudomonas mendocina KR1 Biotechnol Bioeng 90 85 94
61. R Ullrich M Hofrichter 2007 Enzymatic hydroxylation of aromatic compounds Cell Mol Life Sci 64 271 293
62. Urlacher VB, Schmid RD (2007) Modern biooxidation: enzymes, reactions and applications. Wiley-VCH, Stuttgart
63. JB van Beilen Z Li 2002 Enzyme technology: an overview Curr Opin Biotechnol 13 338 344
64. JB van Beilen WA Duetz A Schmid B Witholt 2003 Practical issues in the application of oxygenases Trends Biotechnol 21 170 177
65. G Vardar TK Wood 2004 Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone and pyrogallol Appl Environ Microbiol 70 3253 3262
66. Wackett LP, Hershberger CD (2001) Biocatalysis and biodegradation: microbial transformation of organic compounds, 1st edn. ASM Press, Washington, DC
67. A Wentzel TE Ellingsen H-K Kotlar SB Zotchev M Throne-Holst 2007 Bacterial metabolism of long-chain n-alkanes Appl Microbiol Biotechnol 76 1209 1221
68. GM Whited DT Gibson 1991 Separation and partial purification characterisation of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1 J Bacteriol 173 3017 3020
69. MG Wubbolts P Reuvekamp B Witholt 1994 TOL plasmid-specified xylene oxygenase is a wide substrate range monooxygenase capable of olefin epoxidation Enzyme Microb Technol 16 608 615