Recent advances in oxygenase-catalyzed biotransformations

Current Opinion in Chemical Biology

Volumn 10, Issue 2, 2006, Pages 156-161

  Urlacher, Vlada B ^a   Schmid, Rolf D ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DIOXYGENASE; FLAVOPROTEIN; HEME; ORGANIC COMPOUND; OXYGENASE; STYRENE DERIVATIVE;

BAEYER VILLIGER REACTION; BIOTRANSFORMATION; CATALYSIS; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; EPOXIDATION; HYDROXYLATION; NONHUMAN; OXIDATION; PROTEIN ENGINEERING; PROTEIN FUNCTION; PROTEIN STRUCTURE; REVIEW;

BIOTRANSFORMATION; CATALYSIS; OXYGENASES;

EID: 33645244308     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2006.02.001     Document Type: Review

References (53)

1. A. Schmid, J.S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, and B. Witholt Industrial biocatalysis today and tomorrow Nature 409 2001 258 268
2. J.B. van Beilen, W.A. Duetz, A. Schmid, and B. Witholt Practical issues in the application of oxygenases Trends Biotechnol 21 2003 170 177
3. B. Buhler, and A. Schmid Process implementation aspects for biocatalytic hydrocarbon oxyfunctionalization J Biotechnol 113 2004 183 210 This review summarizes recent advances in the in vivo application of oxygenases. Critical aspects such as low enzyme activity, low enzyme expression rates, product degradation and others are discussed. The authors give some interesting process examples from industry and academia.
4. F.P. Guengerich Cytochrome P450 enzymes in the generation of commercial products Nat Rev Drug Discov 1 2002 359 366
5. V.M. Breinholt, S.E. Rasmussen, K. Brosen, and T.H. Friedberg In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s Pharmacol Toxicol 93 2003 14 22
6. R.B. Vail, M.J. Homann, I. Hanna, and A. Zaks Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPH-P450 reductase expressed in Escherichia coli J Ind Microbiol Biotechnol 32 2005 67 74
7. M.B. Nthangeni, P. Urban, D. Pompon, M.S. Smit, and J.M. Nicaud The use of Yarrowia lipolytica for the expression of human cytochrome P450 CYP1A1 Yeast 21 2004 583 592
8. M. Dietrich, L. Grundmann, K. Kurr, L. Valinotto, T. Saussele, R.D. Schmid, and S. Lange Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris ChemBioChem 6 2005 2014 2022
9. D. Kim, and F.P. Guengerich Enhancement of 7-methoxyresorufin O-demethylation activity of human cytochrome P450 1A2 by molecular breeding Arch Biochem Biophys 432 2004 102 108
10. M. Morant, S. Bak, B.L. Moller, and D. Werck-Reichhart Plant cytochromes P450: tools for pharmacology, plant protection and phytoremediation Curr Opin Biotechnol 14 2003 151 162
11. A.W. Munro, D.G. Leys, K.J. McLean, K.R. Marshall, T.W. Ost, S. Daff, C.S. Miles, S.K. Chapman, D.A. Lysek, and C.C. Moser P450 BM3: the very model of a modern flavocytochrome Trends Biochem Sci 27 2002 250 257
12. W.T. Sulistyaningdyah, J. Ogawa, Q.S. Li, C. Maeda, Y. Yano, R.D. Schmid, and S. Shimizu Hydroxylation activity of P450 BM-3 mutant F87V towards aromatic compounds and its application to the synthesis of hydroquinone derivatives from phenolic compounds Appl Microbiol Biotechnol 67 2005 556 562
13. V.B. Urlacher, A. Makhsumkhanov, and R.D. Schmid Biotransformation of beta-ionone by engineered cytochrome P450 BM-3 Appl Microbiol Biotechnol 2005 1 7
14. D.F. Munzer, P. Meinhold, M.W. Peters, S. Feichtenhofer, H. Griengl, F.H. Arnold, A. Glieder, and A. de Raadt Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3 Chem Commun (Camb) 28 2005 2597 2599
15. P. Meinhold, M.W. Peters, M.M. Chen, K. Takahashi, and F.H. Arnold Direct conversion of ethane to ethanol by engineered cytochrome P450 BM3 ChemBioChem 6 2005 1765 1768 CYP102A1 monooxygenase, an enzyme highly active in fatty acid subterminal oxidation, has been evolved, via directed evolution, into an ethane-hydroxylating enzyme.
16. T. Kubo, M.W. Peters, P. Meinhold, and F.H. Arnold Enantioselective epoxidation of terminal alkenes to (R)- and (S)-epoxides by engineered cytochromes P450 BM-3 Chemistry 12 2006 1216 1220
17. R.J. Sowden, S. Yasmin, N.H. Rees, S.G. Bell, and L.L. Wong Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3 Org Biomol Chem 3 2005 57 64
18. A. Glieder, E.T. Farinas, and F.H. Arnold Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase Nat Biotechnol 20 2002 1135 1139
19. M.W. Peters, P. Meinhold, A. Glieder, and F.H. Arnold Regio- and enantioselective alkane hydroxylation with engineered cytochromes P450 BM-3 J Am Chem Soc 125 2003 13442 13450
20. F. Xu, S.G. Bell, J. Lednik, A. Insley, Z.H. Rao, and L.L. Wong The heme monooxygenase cytochrome P450(cam) can be engineered to oxidize ethane to ethanol Angew Chem Int Ed 44 2005 4029 4032 A clever structure-based protein engineering approach which, by decreasing the size of the substrate binding pocket, turns camphor-selective CYP101 into a fairly active ethane-hydroxylating enzyme.
21. A. Celik, D. Sperandio, R.E. Speight, and N.J. Turner Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450(BM3) from Bacillus megaterium Org Biomol Chem 3 2005 2688 2690
22. S.C. Maurer, K. Kuhnel, L.A. Kaysser, S. Eiben, R.D. Schmid, and V.B. Urlacher Catalytic hydroxylation in biphasic systems using CYP102A1 mutants Adv Synth Catal 347 2005 1090 1098 Isolated CYP102 mutant enzymes are able to transform cyclohexane or fatty acids in a biphasic system into cyclohexanol or hydroxyl fatty acids for several days, using NADH and formate dehydrogenase for cofactor regeneration after protein engineering of the reductase domain.
23. A. Schmid, K. Hofstetter, H.J. Feiten, F. Hollmann, and B. Witholt Integrated biocatalytic synthesis on gram scale: The highly enantioselective preparation of chiral oxiranes with styrene monooxygenase Adv Synth Catal 343 2001 732 737
24. K. Hofstetter, J. Lutz, I. Lang, B. Witholt, and A. Schmid Coupling of biocatalytic asymmetric epoxidation with NADH regeneration in organic-aqueous emulsions Angew Chem Int Ed Engl 43 2004 2163 2166
25. F. Hollmann, P.C. Lin, B. Witholt, and A. Schmid Stereospecific biocatalytic epoxidation: the first example of direct regeneration of a FAD-dependent monooxygenase for catalysis J Am Chem Soc 125 2003 8209 8217 Styrene monooxygenase, a flavin-containing monooxygenase from Pseudomonas sp., forms chiral epoxides in good yields from a wide range of aromatic substrates such as styrol in the presence of a metal-organic mediator that can be regenerated by formate.
26. F. Hollmann, K. Hofstetter, T. Habicher, B. Hauer, and A. Schmid Direct electrochemical regeneration of monooxygenase subunits for biocatalytic asymmetric epoxidation J Am Chem Soc 127 2005 6540 6541
27. A. Meyer, M. Held, A. Schmid, H.P. Kohler, and B. Witholt Synthesis of 3-tert-butylcatechol by an engineered monooxygenase Biotechnol Bioeng 81 2003 518 524
28. N.M. Kamerbeek, D.B. Janssen, W.J.H. van Berkel, and M.W. Fraaije Baeyer-Villiger monooxygenases, an emerging family of flavin-dependent biocatalysts Adv Synth Catal 345 2003 667 678
29. I. Hilker, M.C. Gutierrez, V. Alphand, R. Wohlgemuth, and R. Furstoss Microbiological transformations 57. Facile and efficient resin-based in situ SFPR preparative-scale synthesis of an enantiopure "unexpected" lactone regioisomer via a Baeyer-Villiger oxidation process Org Lett 6 2004 1955 1958 Based on recombinant strains with overexpressed Baeyer-Villiger monooxygenase, reaction engineering was used to synthesize regioisomeric enantiopure lactones from a bicyclic ketone precursor in preparative scale.
30. •], was scaled up to the kilogram scale using a 50 liter bioreactor. The process has been optimized with respect to bottlenecks identified in downscaled experiments.
31. V. Alphand, G. Carrea, R. Wohlgemuth, R. Furstoss, and J.M. Woodley Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases Trends Biotechnol 21 2003 318 323
32. M.D. Mihovilovic, B. Muller, and P. Stanetty Monooxygenase-mediated Baeyer-Villiger oxidations Eur J Org Chem 2002 3711 3730
33. G. Ottolina, G. de Gonzalo, G. Carrea, and B. Danieli Enzymatic Baeyer-Villiger oxidation of bicyclic diketones Adv Synth Catal 347 2005 1035 1040
34. N.M. Kamerbeek, M.J. Moonen, J.G. Van Der Ven, W.J. Van Berkel, M.W. Fraaije, and D.B. Janssen 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds Eur J Biochem 268 2001 2547 2557
35. S. Colonna, S. Del Sordo, N. Gaggero, G. Carrea, and P. Pasta Enzyme-mediated catalytic asymmetric oxidations Heteroatom Chem 13 2002 467 473
36. S. Colonna, N. Gaggero, G. Carrea, and P. Pasta Oxidation of organic cyclic sulfites to sulfates: a new reaction catalyzed by cyclohexanone monooxygenase Chem Commun 1998 415 416
37. M.C. Gutierrez, R. Furstoss, and W. Alphand Microbiological transformations 60. Enantioconvergent Baeyer-Villiger oxidation via a combined whole cells and ionic exchange resin-catalysed dynamic kinetic resolution process Adv Synth Catal 347 2005 1051 1059
38. M.T. Reetz, B. Brunner, T. Schneider, F. Schulz, C.M. Clouthier, and M.M. Kayser Directed evolution as a method to create enantioselective cyclohexanone monooxygenases for catalysis in Baeyer-Villiger reactions Angew Chem Int Ed Engl 43 2004 4075 4078 Using directed evolution and an automated GC screening on 10000 mutants, cyclohexanone monooxygenases with enantioselectivity exceeding 90% ee were screened.
39. M. Bocola, F. Schulz, F. Leca, A. Vogel, M.W. Fraaije, and M.T. Reetz Converting phenylacetone monooxygenase into phenylcyclohexanone monooxygenase by rational design: towards practical Baeyer-Villiger monooxygenases Adv Synth Catal 347 2005 979 986
40. C. Ferreira-Torres, M. Micheletti, and G.J. Lye Microscale process evaluation of recombinant biocatalyst libraries: application to Baeyer-Villiger monooxygenase catalysed lactone synthesis Bioprocess Biosyst Eng 28 2005 83 93
41. D.R. Boyd, N.D. Sharma, and C.C. Allen Aromatic dioxygenases: molecular biocatalysis and applications Curr Opin Biotechnol 12 2001 564 573
42. R. van der Geize, and L. Dijkhuizen Harnessing the catabolic diversity of rhodococci for environmental and biotechnological applications Curr Opin Microbiol 7 2004 255 261
43. D.H. Pieper Aerobic degradation of polychlorinated biphenyls Appl Microbiol Biotechnol 67 2005 170 191
44. W. Buckel On the road to bioremediation of "dioxin" Chem Biol 12 2005 723 724
45. M.J. Larkin, L.A. Kulakov, and C.C. Allen Biodegradation and Rhodococcus-masters of catabolic versatility Curr Opin Biotechnol 16 2005 282 290
46. K. Pollmann, V. Wray, and D.H. Pieper Chloromethylmuconolactones as critical metabolites in the degradation of chloromethylcatechols: recalcitrance of 2-chlorotoluene J Bacteriol 187 2005 2332 2340
47. J.L. Royo, E. Moreno-Ruiz, A. Cebolla, and E. Santero Stable long-term indigo production by overexpression of dioxygenase genes using a chromosomal integrated cascade expression circuit J Biotechnol 116 2005 113 124
48. D. Kim, J.C. Chae, G.J. Zylstra, Y.S. Kim, S.K. Kim, M.H. Nam, Y.M. Kim, and E. Kim Identification of a novel dioxygenase involved in metabolism of o-xylene, toluene, and ethylbenzene by Rhodococcus sp. strain DK17 Appl Environ Microbiol 70 2004 7086 7092
49. K.Y. Choi, D. Kim, S.C. Koh, J.S. So, J.S. Kim, and E. Kim Molecular cloning and identification of a novel oxygenase gene specifically induced during the growth of Rhodococcus sp. strain T104 on limonene J Microbiol 42 2004 160 162
50. S. Yildirim, T.T. Franko, R. Wohlgemuth, H.P.E. Kohler, B. Witholt, and A. Schmid Recombinant chlorobenzene dioxygenase from Pseudomonas sp P51: A biocatalyst for regioselective oxidation of aromatic nitriles Adv Synth Catal 347 2005 1060 1072 This publication is focused on preparative use of dioxygenase for cis-dihydroxylation of aromatic nitriles. The approach can enable the production of new synthons in significant yields.
51. B.G. Keenan, T. Leungsakul, B.F. Smets, and T.K. Wood Saturation mutagenesis of Burkholderia cepacia R34 2,4-dinitrotoluene dioxygenase at DntAc valine 350 for synthesizing nitrohydroquinone, methylhydroquinone, and methoxyhydroquinone Appl Environ Microbiol 70 2004 3222 3231
52. B.G. Keenan, T. Leungsakul, B.F. Smets, M.A. Mori, D.E. Henderson, and T.K. Wood Protein engineering of the archetypal nitroarene dioxygenase of Ralstonia sp. strain U2 for activity on aminonitrotoluenes and dinitrotoluenes through alpha-subunit residues leucine 225, phenylalanine 350, and glycine 407 J Bacteriol 187 2005 3302 3310
53. C.R. Otey, G. Bandara, J. Lalonde, K. Takahashi, and F.H. Arnold Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450 Biotechnol Bioeng 93 2006 494 499 In this work, variants of CYP102A1 (P450 BM-3) were constructed and described, that are able to accept and convert propranolol, a multi-function β-adrenergic blocker. Implementation of these variants would open up a cost-effective route to the production of different human metabolites.