Cloning, expression and characterisation of CYP102A7, a self-sufficient P450 monooxygenase from Bacillus licheniformis

Applied Microbiology and Biotechnology

Volumn 79, Issue 6, 2008, Pages 931-940

  Dietrich, Matthias ^a   Eiben, Sabine ^a   Asta, Chimene ^a   Do, Tuan Anh ^a   Pleiss, Juergen ^a   Urlacher, Vlada B ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Bacillus licheniformis; CYP102A; Cytochrome P450 monooxygenases; Self sufficient

Indexed keywords

ACIDS; BACTERIOLOGY; BIOCHEMICAL ENGINEERING; CARBOXYLIC ACIDS; CLONING; GENETIC ENGINEERING; HYDROCARBONS; LIPIDS; MICROFLUIDICS; OLEFINS; PORPHYRINS; PROTEINS;

BACILLUS LICHENIFORMIS; CATALYSE; CHARACTERISATION; COUPLING EFFICIENCIES; CYTOCHROME P450 (CYP); FATTY ACID HYDROXYLASES; FUSION PROTEINS; HEME DOMAIN; MEDIUM-CHAIN FATTY ACIDS; MONO OXYGENASES; MONOOXYGENASE; REDUCTASE (BVR-A); UNSATURATED FATTY ACID (UFA);

FATTY ACIDS;

CYTOCHROME P450; UNSPECIFIC MONOOXYGENASE;

BACTERIUM; CATALYSIS; CLONE; CYTOCHROME; ENZYME ACTIVITY; FATTY ACID; OXIDATION; PROTEIN;

ARTICLE; BACILLUS LICHENIFORMIS; CATALYSIS; COUPLING FACTOR; MOLECULAR CLONING; NONHUMAN; OXIDATION; PROTEIN EXPRESSION; THERMOSTABILITY;

BACILLUS; BACTERIAL PROTEINS; BINDING SITES; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME STABILITY; FATTY ACIDS; GENE EXPRESSION; KINETICS; MODELS, MOLECULAR; NADPH-FERRIHEMOPROTEIN REDUCTASE; SUBSTRATE SPECIFICITY;

BACILLUS LICHENIFORMIS;

EID: 46149102464     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-008-1500-8     Document Type: Article

References (36)

1. Appel D, Lutz-Wahl S, Fischer P, Schwaneberg U, Schmid RD (2001) A P450BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. J Biotechnol 88:167-171
2. Boddupalli SS, Oster T, Estabrook RW, Peterson JA (1992) Reconstitution of the fatty acid hydroxylation function of cytochrome P450 BM-3 utilizing its individual recombinant hemo- and flavoprotein domains. J Biol Chem 267:10375-10380
3. Brady GP Jr, Stouten PF (2000) Fast prediction and visualization of protein binding pockets with PASS. J Comput Aided Mol Des 14:383-401
4. Budde M, Maurer SC, Schmid RD, Urlacher VB (2004) Cloning, expression and characterisation of CYP102A2, a self-sufficient P450 monooxygenase from Bacillus subtilis. Appl Microbiol Biotechnol 66:180-186
5. Budde M, Morr M, Schmid RD, Urlacher VB (2006) Selective hydroxylation of highly branched fatty acids and their derivatives by CYP102A1 from Bacillus megaterium. Chembiochem 7:789-794
6. Capdevila JH, Wei S, Helvig C, Falck JR, Belosludtsev Y, Truan G, Graham-Lorence SE, Peterson JA (1996) The highly stereoselective oxidation of polyunsaturated fatty acids by cytochrome P450 BM-3. J Biol Chem 271:22663-22671
7. Chowdhary PK, Alemseghed M, Haines DC (2007a) Cloning, expression and characterization of a fast self-sufficient P450: CYP102A5 from Bacillus cereus. Arch Biochem Biophys 468:32-43
8. Chowdhary PK, Keshavan N, Nguyen HQ, Peterson JA, Gonzalez JE, Haines DC (2007b) Bacillus megaterium CYP102A1 oxidation of acyl homoserine lactones and acyl homoserines. Biochemistry 46:14429-14437
9. DeLano WL (2005) The case for open-source software in drug discovery. Drug Discov Today 10:213-217
10. Eiben S, Bartelmas H, Urlacher VB (2007) Construction of a thermostable cytochrome P450 chimera derived from self-sufficient mesophilic parents. Appl Microbiol Biotechnol 75:1055-1061
11. Guex N, Peitsch MC (1997) SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling. Electrophoresis 18:2714-2723
12. Gustafsson MC, Roitel O, Marshall KR, Noble MA, Chapman SK, Pessegueiro A, Fulco AJ, Cheesman MR, von Wachenfeldt C, Munro AW (2004) Expression, purification, and characterization of Bacillus subtilis cytochromes P450 CYP102A2 and CYP102A3: flavocytochrome homologues of P450 BM3 from Bacillus megaterium. Biochemistry 43:5474-5487
13. Haines DC, Tomchick DR, Machius M, Peterson JA (2001) Pivotal role of water in the mechanism of P450BM-3. Biochemistry 40:13456-13465
14. Hannemann F, Bichet A, Ewen KM, Bernhardt R (2007) Cytochrome P450 systems-biological variations of electron transport chains. Biochim Biophys Acta 1770:330-344
15. Isin EM, Guengerich FP (2007) Complex reactions catalyzed by cytochrome P450 enzymes. Biochim Biophys Acta 1770:314-329
16. Joyce MG, Girvan HM, Munro AW, Leys D (2004) A single mutation in cytochrome P450 BM3 induces the conformational rearrangement seen upon substrate binding in the wild-type enzyme. J Biol Chem 279:23287-23293
17. Kim BS, Kim SY, Park J, Park W, Hwang KY, Yoon YJ, Oh WK, Kim BY, Ahn JS (2007) Sequence-based screening for self-sufficient P450 monooxygenase from a metagenome library. J Appl Microbiol 102:1392-1400
18. Kuehnel K, Maurer SC, Galeyeva Y, Frey W, Laschat S, Urlacher VB (2007) Hydroxylation of dodecanoic acid and (2R,4R,6R,8R)-tetramethyldecanol on a preparative scale using an NADH-dependent CYP102A1 mutant. Adv Synth Catal 349:1451-1461
19. Lentz O, Urlacher V, Schmid RD (2004) Substrate specificity of native and mutated cytochrome P450 (CYP102A3) from Bacillus subtilis. J Biotechnol 108:41-49
20. Li H, Poulos TL (1997) The structure of the cytochrome P450BM-3 haem domain complexed with the fatty acid substrate, palmitoleic acid. Nat Struct Biol 4:140-146
21. Liu L, Schmid RD, Urlacher VB (2006) Cloning, expression, and characterization of a self-sufficient cytochrome P450 monooxygenase from Rhodococcus ruber DSM 44319. Appl Microbiol Biotechnol 72:876-882
22. Maurer S, Urlacher V, Schulze H, Schmid RD (2003) Immobilisation of P450 BM-3 and an NADP+ cofactor recycling system: towards a technical application of heme-containing monooxygenases in fine chemical synthesis. Adv Synth Catal 345:802-810
23. Narhi LO, Fulco AJ (1987) Identification and characterization of 2 functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium. J Biol Chem 262:6683-6690
24. Narhi LO, Wen LP, Fulco AJ (1988) Characterization of the protein expressed in Escherichia coli by a recombinant plasmid containing the Bacillus megaterium cytochrome P-450BM-3 gene. Mol Cell Biochem 79:63-71
25. Noble MA, Miles CS, Chapman SK, Lysek DA, MacKay AC, Reid GA, Hanzlik RP, Munro AW (1999) Roles of key active-site residues in flavocytochrome P450 BM3. Biochem J 339(Pt 2):371-379
26. Omura T, Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239:2379-2385
27. Ortiz de Montellano P (2005) Cytochrome P450: structure, mechanism and biochemistry, 3rd edn. Springer, The Netherlands
28. Ost TW, Munro AW, Mowat CG, Taylor PR, Pesseguiero A, Fulco AJ, Cho AK, Cheesman MA, Walkinshaw MD, Chapman SK (2001) Structural and spectroscopic analysis of the F393H mutant of flavocytochrome P450 BM3. Biochemistry 40:13430-13438
29. Ravichandran KG, Boddupalli SS, Hasemann CA, Peterson JA, Deisenhofer J (1993) Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450s. Science 261:731-736
30. Roberts GA, Celik A, Hunter DJ, Ost TW, White JH, Chapman SK, Turner NJ, Flitsch SL (2003) A self-sufficient cytochrome P450 with a primary structural organization that includes a flavin domain and a [2Fe-2S] redox center. J Biol Chem 278:48914-48920
31. Schwaneberg U, Schmidt-Dannert C, Schmitt J, Schmid RD (1999) A continuous spectrophotometric assay for P450 BM-3, a fatty acid hydroxylating enzyme, and its mutant F87A. Anal Biochem 269:359-366
32. Schwede T, Kopp J, Guex N, Peitsch MC (2003) SWISS-MODEL: An automated protein homology-modeling server. Nucleic Acids Res 31:3381-3385
33. Sowden RJ, Yasmin S, Rees NH, Bell SG, Wong LL (2005) Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3. Org Biomol Chem 3:57-64
34. Urlacher VB, Makhsumkhanov A, Schmid RD (2006) Biotransformation of beta-ionone by engineered cytochrome P450 BM-3. Appl Microbiol Biotechnol 70:53-59
35. Watanabe Y, Laschat S, Budde M, Affolter O, Shimada Y, Urlacher VB (2007) Oxidation of acyclic monoterpenes by P450 BM-3 monooxygenase: influence of the substrate E/Z-isomerism on enzyme chemo- and regioselectivity. Tetrahedron 63:9413-9422
36. Wen LP, Fulco AJ (1987) Cloning of the gene encoding a catalytically self-sufficient cytochrome P-450 fatty acid monooxygenase induced by barbiturates in Bacillus megaterium and its functional expression and regulation in heterologous (Escherichia coli) and homologous (Bacillus megaterium) hosts. J Biol Chem 262:6676-6682