Insights in the kinetic mechanism of the eukaryotic Baeyer-Villiger monooxygenase BVMOAf1 from Aspergillus fumigatus Af293

Biochimie

Volumn 107, Issue PB, 2014, Pages 270-276

  Mascotti, María Laura ^a   Kurina Sanz, Marcela ^a   Juri Ayub, Maximiliano ^a   Fraaije, Marco W ^b  

^a UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Aspergillus fumigatus; Baeyer Villiger monooxygenases; BVMOAf1; Kinetic mechanism; Site directed mutagenesis

Indexed keywords

BAEYER VILLIGER MONOOXYGENASE; FUNGAL ENZYME; HYDROGEN PEROXIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; QUERCETIN DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SODIUM DITHIONITE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; FUNGAL PROTEIN; MIXED FUNCTION OXIDASE; RIBOFLAVIN DERIVATIVE;

ABSORPTION SPECTROPHOTOMETRY; AMINO ACID SUBSTITUTION; ARTICLE; ASPERGILLUS FUMIGATUS; BAEYER VILLIGER REACTION; CATALYSIS; COENZYME; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DISSOCIATION CONSTANT; KINETICS; NONHUMAN; OXIDATION REDUCTION STATE; SITE DIRECTED MUTAGENESIS; STEADY STATE; STEREOSPECIFICITY; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; OXIDATION REDUCTION REACTION; PROTEIN CONFORMATION; PROTEIN TERTIARY STRUCTURE;

ASPERGILLUS FUMIGATUS; ASPERGILLUS FUMIGATUS AF293; EUKARYOTA;

ASPERGILLUS FUMIGATUS; BINDING SITES; CATALYSIS; FLAVINS; FUNGAL PROTEINS; KINETICS; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; NADP; OXIDATION-REDUCTION; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY;

EID: 84915811281     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2014.09.005     Document Type: Article

References (39)

1. V. Joosten, and W.J.H. van Berkel Flavoenzymes Curr. Opin. Chem. Biol. 11 2007 195 202
2. D.E. Torres Pazmiño, M. Winkler, A. Glieder, and M.W. Fraaije Monooxygenases as biocatalysts: classification, mechanistic aspects and biotechnological applications J. Biotechnol. 146 2010 9 24
3. D.E. Torres Pazmiño, H.M. Dudek, and M.W. Fraaije Baeyer-Villiger monooxygenases: recent advances and future challenges Curr. Opin. Chem. Biol. 14 2009 1 7
4. H. Leisch, K. Morley, and P.C.K. Lau Baeyer-Villiger monooxygenases: more than just green chemistry Chem. Rev. 111 2011 4165 4222
5. G. de Gonzalo, D.E. Torres Pazmiño, G. Ottolina, M.W. Fraaije, and G. Carrea Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca Tet. Asymm. 16 2005 3077 3083
6. G. de Gonzalo, M.D. Mihovilovic, and M.W. Fraaije Recent developments in the application of Baeyer-Villiger monooxygenases as biocatalysts ChemBioChem 11 2010 2208 2231
7. M. Kadow, S. Saß, M. Schmidt, and U.T. Bornscheuer Recombinant expression and purification of the 2,5-diketocamphane 1,2-monooxygenase from the camphor metabolizing Pseudomonas putida strain NCIMB 10007 AMB Express 1 2011 13
8. A. Riebel, H.M. Dudek, G. de Gonzalo, P. Stepniak, L. Rychlewski, and M.W. Fraaije Expanding the set of rhodococcal Baeyer-Villiger monooxygenases by high-throughput cloning, expression and substrate screening Appl. Microbiol. Biotechnol. 95 2012 1479 1489
9. H. Leisch, R. Shi, S. Grosse, K. Morley, H. Bergeron, M. Cygler, H. Iwaki, Y. Hasegawa, and P.C.K. Lau Cloning, Baeyer-Villiger biooxidations, and structures of the camphor pathway 2-oxo-3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase of Pseudomonas putida ATCC 17453 Appl. Environ. Microbiol. 78 2012 2200 2212
10. F. Hollmann, A. Taglieber, F. Schulz, and M.T. Reetz A light-driven stereoselective biocatalytic oxidation Angew. Chem. Int. Ed. 16 2007 1 5
11. W.H. Lee, J.B. Park, K. Park, M.D. Kim, and J.H. Seo Enhanced production of caprolactone by overexpression of NADPH-regenerating glucose 6-phosphate dehydrogenase in recombinant Escherichia coli harboring cyclohexanone monooxygenase gene Appl. Microbiol. Biotechnol. 76 2007 329 338
12. S. Staudt, U.T. Bornscheuer, U. Menyesc, W. Hummeld, and H. Gröger Direct biocatalytic one-pot-transformation of cyclohexanol with molecular oxygen into ε-caprolactone Enzyme Microb. Technol. 53 2013 288 292
13. C.M. Clouthier, and M.K. Kayser Increasing the enantioselectivity of cyclopentanone monooxygenase (CPMO): profile of new CPMO mutants Tet. Asymm. 17 2006 2649 2653
14. M.T. Reetz, and S. Wu Laboratory evolution of robust and enantioselective Baeyer-Villiger monooxygenases for asymmetric catalysis J. Am. Chem. Soc. 131 2009 15424 15432
15. D.E. Torres Pazmiño, R. Snajdrova, D.V. Rial, M.D. Mihovilovic, and M.W. Fraaije Altering the substrate specificity and enantioselectivity of phenylacetone monooxygenase by structure-inspired enzyme redesign Adv. Synth. Catal. 348 2007 1361 1368
16. A. Kirschner, and U.T. Bornscheuer Directed evolution of a Baeyer-Villiger monooxygenase to enhance enantioselectivity Appl. Microbiol. Biotechnol. 81 2008 465 472
17. Z.G. Zhang, G.D. Roiban, J.P. Acevedo, I. Polyak, and M.T. Reetz A new type of stereoselectivity in Baeyer-Villiger reactions: access to E- and Z-olefins Adv. Synth. Catal. 355 2013 99 106
18. H.M. Dudek, M.J. Fink, A.V. Shivange, A. Dennig, M.D. Mihovilovic, U. Schwaneberg, and M.W. Fraaije Extending the substrate scope of a Baeyer-Villiger monooxygenase by multiple-site mutagenesis Appl. Microbiol. Biotechnol. 2013 10.1007/s00253-013-5364-1
19. C. Cummings Ryerson, D.P. Ballou, and C. Walsh Mechanistic studies on cyclohexanone oxygenase Biochemistry 21 1982 2644 2655
20. D. Sheng, D.P. Ballou, and V. Massey Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis Biochemistry 40 2001 11156 11167
21. D.E. Torres Pazmiño, B.J. Baas, D.B. Janssen, and M.W. Fraaije Kinetic mechanism of phenylacetone monooxygenase from Thermobifida fusca Biochemistry 47 2008 4082 4093
22. A. Riebel, M.J. Fink, M.D. Mihovilovic, and M.W. Fraaije Type II flavin-containing monooxygenases: a new class of biocatalysts that harbors Baeyer-Villiger monooxygenases with a relaxed coenzyme specificity ChemCatChem 2013 10.1002/cctc.201300550
23. M.L. Mascotti, M. Juri Ayub, H.M. Dudek, M. Kurina Sanz, and M.W. Fraaije Cloning, overexpression and biocatalytic exploration of a novel Baeyer-Villiger monooxygenase from Aspergillus fumigatus Af293 AMB Express 3 2013 1 10
24. D.E. Torres Pazmiño, A. Riebel, J. De Lange, F. Rudroff, M.D. Mihovilovic, and M.W. Fraaije Efficient biooxidations catalyzed by a new generation of self-sufficient Baeyer-Villiger monooxygenases ChemBioChem 10 2009 2595 2598
25. T. Ozaki, S. Mishima, M. Nishiyama, and T. Kuzuyama NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids J. Antibiot. 62 2009 385 392
26. P. Thordarson Determining association constants from titration experiments in supramolecular chemistry Chem. Soc. Rev. 40 2011 1305 1323
27. N.B. Beaty, and D.P. Ballou The reductive half-reaction of liver microsomal FAD-containing monooxygenase J. Biol. Chem. 256 1981 4611 4618
28. CPHmodels 3.2 Server. Available from: www.cbs.dtu.dk/services/CPHmodels.
29. E. Malito, A. Alfieri, M.W. Fraaije, and A. Mattevi Crystal structure of a Baeyer-Villiger monooxygenase Proc. Natl. Acad. Sci. USA 101 2004 13157 13162
30. N.M. Kamerbeek, M.W. Fraaije, and D.B. Janssen Identifying determinants of NADPH specificity in Baeyer-Villiger monooxygenases Eur. J. Biochem. 271 2004 2107 2116
31. R. Orru, H.M. Dudek, C. Martinoli, D.E. Torres Pazmiño, A. Royant, M. Weik, M.W. Fraaije, and A. Mattevi Snapshots of enzymatic Baeyer-Villiger catalysis. Oxygen activation and intermediate stabilization J. Biol. Chem. 286 2011 29284 29291
32. M.W. Fraaije, N.M. Kamerbeek, W.J.H. van Berkel, and D.B. Janssen Identification of a Baeyer-Villiger monooxygenase sequence motif FEBS Lett. 518 2002 43 47
33. M.J. Cheesman, M.B. Kneller, and A.B. Rettie Critical role of histidine residues in cyclohexanone monooxygenase expression, cofactor binding and catalysis Chem. Biol. Interact. 146 2003 157 164
34. D.E. Torres Pazmiño, and M.W. Fraaije Discovery, redesign and applications of Baeyer-Villiger monooxygenases M. Tomoko, Future Directions in Biocatalysis 2007 Elsevier BV New York, USA 107 127
35. F. Leipold, R. Wardernga, and U.T. Bornscheuer Cloning, expression and characterization of a eukaryotic cycloalkanone monooxygenase from Cylindrocarpon radicicola ATCC 11011 Appl. Microbiol. Biotechnol. 94 2011 705 712
36. T. Itoh, K. Tokunaga, Y. Matsuda, I. Fujii, I. Abe, Y. Ebizuka, and T. Kushiro Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases Nat. Chem. 2 2010 858 864
37. D. Boettger, and C. Hertweck Molecular diversity sculpted by fungal PKS-NRPS hybrids ChemBioChem 14 2013 28 42
38. P. Chaiyen, M.W. Fraaije, and A. Mattevi The enigmatic reaction of flavins with oxygen Trends Biochem. Sci. 37 2012 373 380
39. P. Wiemann, C.J. Guob, J.M. Palmer, R. Sekonyelac, C.C.C. Wang, and N.P. Keller Prototype of an intertwined secondary-metabolite supercluster Proc. Natl. Acad. Sci. USA 110 2013 17065 17070