Identification and characterization of 4-hexylbenzoic acid and 4-nonyloxybenzoic acid as substrates of CYP102A1

Applied Microbiology and Biotechnology

Volumn 90, Issue 1, 2011, Pages 117-126

  Gudiminchi, Rama Krishna ^a   Smit, Martha Sophia ^a  

^a UNIVERSITY OF THE FREE STATE   (South Africa)

Author keywords

4 Hexylbenzoic acid; 4 Nonyloxybenzoic acid; CYP102A1; Fluorescence based oxygen consumption; P450 BM 3; Substrate screening; Whole cell biotransformation

Indexed keywords

4-HEXYLBENZOIC ACID; 4-NONYLOXYBENZOIC ACID; CYP102A1; P450 BM-3; WHOLE-CELL BIOTRANSFORMATIONS;

BIOSENSORS; CELLS; FLUORESCENCE; OXYGEN; SUBSTRATES;

FATTY ACIDS;

4 HEXYLBENZOIC ACID; 4 NONYLOXYBENZOIC ACID; BENZOIC ACID; CYTOCHROME P450 BM3; OMEGA 1 HYDROXYHEXYLBENZOIC ACID; OMEGA 2 HYDROXYHEXYLBENZOIC ACID; OMEGA 2 HYDROXYNONYLOXYBENZOIC ACID; OMEGA 2,OMEGA 4 DIHYDROXYNONYLOXYBENZOIC ACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

BIOTRANSFORMATION; CHEMICAL BINDING; ENZYME ACTIVITY; FATTY ACID; OXYGEN; SENSOR; SPECTROSCOPY; SUBSTRATE;

ARTICLE; BIOTRANSFORMATION; ENZYME SUBSTRATE; ESCHERICHIA COLI; NONHUMAN; WHOLE CELL;

BACILLUS MEGATERIUM; BACTERIAL PROTEINS; BENZOIC ACID; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; KINETICS; MOLECULAR STRUCTURE; NADPH-FERRIHEMOPROTEIN REDUCTASE; SUBSTRATE SPECIFICITY;

EID: 79954748700     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-3029-x     Document Type: Article

References (35)

1. Barrow SE, Taylor GW (1987) Gas chromatography and mass spectrometry of eicosanoids. In: Benedetto C, McDonald-Gibson RG, Nigam S, Slater TF (eds) Prostaglandins and related compounds: a practical approach series. IRL, Oxford, pp 99-141
2. BM-3 J Biol Chem 265 4233 4239 1:CAS:528: DyaK3cXhsFChtL8%3D
3. SS Boddupalli BC Pramanik CA Slaughter RW Estabrook JA Peterson 1992 Fatty acid monooxygenation by P450BM-3: product identification and proposed mechanism for sequential hydroxylation Arch Biochem Biophys 292 20 28 10.1016/0003-9861(92)90045-X 1:CAS:528:DyaK38Xjs1yhsQ%3D%3D
4. M Budde M Morr RD Schmid VB Urlacher 2006 Selective hydroxylation of highly branched fatty acids and their derivatives by CYP102A1 from Bacillus megaterium Chembiochem 7 789 794 10.1002/cbic.200500444 1:CAS:528: DC%2BD28Xkslygsro%3D (Pubitemid 43764188)
5. S-J Choi M Kim SI Kim J-K Jeon 2003 Microplate assay measurement of cytochrome P450-carbon monoxide complexes J Biochem Mol Biol 36 332 335 1:CAS:528:DC%2BD3sXkslCgtLs%3D (Pubitemid 36890834)
6. BM3 Tetrahedron Lett 48 133 136 10.1016/j.tetlet.2006.10.136 1:CAS:528:DC%2BD28Xht1yktrfJ (Pubitemid 44821268)
7. Eiben S (2007) CYP102A P450 monooxygenases: comparative analysis and construction of cytochrome P450 chimeras. Thesis, University of Stuttgart
8. S Eiben L Kaysser S Maurer K Kühnel VB Urlacher RD Schmid 2006 Preparative use of isolated CYP102 monooxygenases-a critical appraisal J Biotechnol 124 662 669 10.1016/j.jbiotec.2006.02.013 1:CAS:528: DC%2BD28XntlClu7c%3D (Pubitemid 44066594)
9. T Fujii T Narikawa F Sumisa A Arisawa K Takeda J Kato 2006 Production of α, ω-alkanediols using Escherichia coli expressing a cytochrome P450 from Acinetobacter sp. OC4 Biosci Biotechnol Biochem 70 1379 1385 10.1271/bbb.50656 1:CAS:528:DC%2BD28XmslWktbs%3D (Pubitemid 43961814)
10. S Graham-Lorence G Truan JA Peterson JR Falck S Wei C Helvig JH Capdevila 1997 An active site substitution, F87V, converts cytochrome P450 BM-3 into a regio- and stereoselective (14S, 15R)-arachidonic acid epoxygenase J Biol Chem 272 1127 1135 10.1074/jbc.272.2.1127 1:CAS:528:DyaK2sXmtFKhug%3D%3D (Pubitemid 27034608)
11. HM Girvan KR Marshall RJ Lawson D Leys MG Joyce J Clarkson WE Smith MR Cheesman AW Munro 2004 Flavocytochrome P450 BM3 mutant A264E undergoes substrate-dependent formation of a novel heme iron ligand set J Biol Chem 279 23274 23286 10.1074/jbc.M401716200 1:CAS:528:DC%2BD2cXkt1Gisbc%3D (Pubitemid 38685636)
12. W-C Huang ACG Westlake J-D Maréchal MG Joyce PCE Moody GCK Roberts 2007 Filling a hole in cytochrome P450 BM3 improves substrate binding and catalytic efficiency J Mol Biol 373 633 651 10.1016/j.jmb.2007.08.015 1:CAS:528:DC%2BD2sXhtFelsbbN (Pubitemid 47488398)
13. Q-S Li J Ogawa RD Schmid S Shimizu 2001 Residue size at position 87 of cytochrome P450 BM-3 determines its stereoselectivity in propylbenzene and 3-chlorostyrene oxidation FEBS Lett 508 249 252 10.1016/S0014-5793(01)03074-5 1:CAS:528:DC%2BD3MXosFKqt78%3D (Pubitemid 33079255)
14. SC Maurer K Kühnel LA Kaysser S Eiben RD Schmid VB Urlacher 2005 Catalytic hydroxylation in biphasic systems using CYP102A1 mutants Adv Synth Catal 347 1090 1098 10.1002/adsc.200505044 1:CAS:528:DC%2BD2MXlsV2gsbw%3D (Pubitemid 40840030)
15. 450cam Biochemistry 34 8982 8988 10.1021/bi00028a006 1:CAS:528:DyaK2MXmsFCrs7k%3D
16. T Mouri J Michizoe H Ichinose N Kamiya M Goto 2006 A recombinant Escherichia coli whole cell biocatalyst harbouring a cytochrome P450cam monooxygenase system coupled with enzymatic cofactor regeneration Appl Microbiol Biotechnol 72 514 520 10.1007/s00253-005-0289-y 1:CAS:528:DC%2BD28XotlChsrY%3D (Pubitemid 44273078)
17. LO Narhi AJ Fulco 1982 Phenobarbital induction of a soluble cytochrome P-450-dependent fatty-acid mono-oxygenase in Bacillus megaterium J Biol Chem 257 2147 2150 1:CAS:528:DyaL38XhvFKgsro%3D (Pubitemid 12069765)
18. MA Noble CS Miles SK Chapman DA Lysek AC Mackay GA Reid RP Hanzlik AW Munro 1999 Roles of key active-site residues in flavocytochrome P450BM3 Biochem J 339 371 379 10.1042/0264-6021:3390371 1:CAS:528:DyaK1MXjtVaktL0%3D (Pubitemid 29209968)
19. A Olry F Schneider-Belhaddad D Heintz D Werck-Reichhart 2007 A medium-throughput screening assay to determine catalytic activities of oxygen-consuming enzymes: a new tool for functional characterization of cytochrome P450 and other oxygenases Plant J 51 331 340 10.1111/j.1365-313X. 2007.03140.x 1:CAS:528:DC%2BD2sXosFCnsbs%3D (Pubitemid 47030125)
20. T Omura R Sato 1964 Carbon monoxide-binding pigment of liver microsomes J Biol Chem 239 2370 2378 1:CAS:528:DyaF2cXktF2gur4%3D
21. TW Ost CS Miles J Murdoch Y Cheung GA Reid SK Chapman AW Munro 2000 Rational re-design of the substrate binding site of flavocytochrome P450 BM3 FEBS Lett 486 173 177 10.1016/S0014-5793(00)02267-5 1:CAS:528: DC%2BD3cXoslGhs7s%3D
22. S Pflug SM Richter VB Urlacher 2007 Development of a fed-batch process for the production of the cytochrome P450 monooxygenase CYP102A1 from Bacillus megaterium in E. coli J Biotechnol 129 481 488 10.1016/j.jbiotec.2007.01.013 1:CAS:528:DC%2BD2sXktFyqtrg%3D (Pubitemid 46560159)
23. KG Ravichandran SS Boddupalli CA Hasermann JA Peterson J Deisenhofer 1993 Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's Science 261 731 736 10.1126/science.8342039 1:CAS:528:DyaK3sXlslKmur4%3D (Pubitemid 23278388)
24. AP Rolo MC Palmeira AG Cortopassi 2009 Biosensor plates detect mitochondrial physiological regulators and mutations in vivo Anal Biochem 385 176 178 10.1016/j.ab.2008.10.002 1:CAS:528:DC%2BD1cXhsFCmsbzM
25. Sambrook J, Fritsch EF, Maniatis T (1989) Molecular cloning: a laboratory manual, 2nd edn. Cold Spring Harbor Laboratory Press, New York
26. BM-3 Monooxygenase Appl Environ Microbiol 64 3784 3790 1:CAS:528:DyaK1cXms1ent7Y%3D (Pubitemid 28462973)
27. S Schneider MG Wubbolts G Oesterhelt D Sanglard B Witholt 1999 Controlled regioselectivity of fatty acid oxidation by whole cells producing cytochrome P450BM-3 monooxygenase under varied dissolved oxygen concentrations Biotechnol Bioeng 64 333 341 10.1002/(SICI)1097-0290(19990805)64:3<333::AID-BIT9>3.0. CO;2-2 1:CAS:528:DyaK1MXktVymsbw%3D (Pubitemid 29297386)
28. MS Smit MM Mokgoro E Setati JM Nicaud 2005 α, ω-Dicarboxylic acid accumulation by acyl-CoA oxidase deficient mutants of Yarrowia lipolytica Biotechnol Lett 27 859 864 10.1007/s10529-005-6719-1 1:CAS:528: DC%2BD2MXntVehtLw%3D (Pubitemid 41175431)
29. RJ Sowden S Yasmin NH Rees SG Bell L-L Wong 2005 Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3 Org Biomol Chem 3 57 64 10.1039/b413068e 1:CAS:528:DC%2BD2cXhtVylt7vJ (Pubitemid 40086162)
30. GE Tsotsou AEG Cass G Gilardi 2002 High throughput assay for cytochrome P450 BM3 for screening libraries of substrates and combinatorial mutants Biosens Bioelectron 17 119 131 10.1016/S0956-5663(01)00285-8 1:CAS:528: DC%2BD3MXptVSmu74%3D (Pubitemid 34003618)
31. LP Wen AJ Fulco 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 1:CAS:528:DyaL2sXktFyrtL4%3D
32. CJC Whitehouse SG Bell HG Tufton RJP Kenny LCI Ogilvie L-L Wong 2008 Evolved CYP102A1 (P450BM3) variants oxidise a range of non-natural substrates and offer new selectivity options Chem Commun 8 966 968 10.1039/b718124h (Pubitemid 351281049)
33. BM3 (CYP102A1) Chem Eur J 14 10905 10908 10.1002/chem.200801927 1:CAS:528:DC%2BD1MXpsFeh
34. CJC Whitehouse SG Bell W Yang JA Yorke CF Blanford AJF Strong EJ Morse M Bartlam Z Rao LL Wong 2009 A highly active single-mutation variant of P450BM3 (CYP102A1) Chembiochem 10 1654 1656 10.1002/cbic.200900279 1:CAS:528: DC%2BD1MXosVegu74%3D
35. M Wodnicka RD Guarino JJ Hemperly MR Timmins D Stitt JB Pitner 2000 Novel fluorescent technology platform for high throughput cytotoxicity and proliferation assays Biomol Screen 5 141 152 10.1177/108705710000500306 1:STN:280:DC%2BD3czos1arug%3D%3D