Selective steroid oxyfunctionalisation by CYP154C5, a bacterial cytochrome P450

Microbial Cell Factories

Volumn 12, Issue 1, 2013, Pages

  Bracco, Paula ^a   Janssen, Dick B ^b   Schallmey, Anett ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

CYP154C5; Cytochrome P450 monooxygenase; Hydroxypropyl cyclodextrin; Nocardia farcinica IFM 10152; Regioselective; Stereoselective; Steroid hydroxylation; Whole cell catalysis

Indexed keywords

ANDROSTENEDIONE; BACTERIAL PROTEIN; CYTOCHROME P450; CYTOCHROME P450 154C5; MEMBRANE PROTEIN; NANDROLONE; PDR PROTEIN; PRASTERONE; PROGESTERONE; PUTIDAREDOXIN; PUTIDAREDOXIN REDUCTASE; TESTOSTERONE; TRANSCRIPTION FACTOR PDX 1; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYST; CHEMICAL STRUCTURE; CLONING; CONTROLLED STUDY; ELECTRON TRANSPORT; ESCHERICHIA COLI; GENE EXPRESSION; NOCARDIA FARCINICA; NONHUMAN; OXIDATION REDUCTION REACTION; PSEUDOMONAS PUTIDA; STEREOCHEMISTRY; STEROID HYDROXYLATION; WHOLE CELL;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NOCARDIA FARCINICA IFM 10152; PSEUDOMONAS PUTIDA;

BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; HYDROXYLATION; OXIDATION-REDUCTION; STEROIDS;

EID: 84885567349     PISSN: None     EISSN: 14752859     Source Type: Journal    
DOI: 10.1186/1475-2859-12-95     Document Type: Article

References (28)

1. Ortiz De Montellano P. Cytochrome P450: structure, mechanism, and biochemistry 2004, New York: Kluwer Academic/Plenum Publisher, 3.
2. Bernhardt R. Cytochromes P450 as versatile biocatalysts. J Biotechnol 2006, 124:128-145. 10.1016/j.jbiotec.2006.01.026, 16516322.
3. Isin EM, Guengerich FP. Complex reactions catalyzed by cytochrome P450 enzymes. BBA-Gen Subjects 2007, 1770:314-329.
4. Bureik M, Bernhardt R, Bureik M, Bernhardt R. Steroid hydroxylation: microbial steroid biotransformations using cytochrome P450 enzymes. Modern Biooxidation 2007, 155-176. Weinheim: Wiley-VCH, Schmid RD, Urlacher VB.
5. Hannemann F, Bichet A, Ewen KM, Bernhardt R. Cytochrome P450 systems-biological variations of electron transport chains. BBA-Gen Subjects 2007, 1770:330-344.
6. Zehentgruber D, Hannemann F, Bleif S, Bernhardt R, Lütz S. Towards preparative scale steroid hydroxylation with cytochrome P450 monooxygenase CYP106A2. ChemBioChem 2010, 11:713-721. 10.1002/cbic.200900706, 20183841.
7. Fernandes P, Cruz A, Angelova B, Pinheiro H, Cabral JM. Microbial conversion of steroid compounds: recent developments. Enzyme Microb Technol 2003, 32:688-705.
8. Donova MV, Egorova OV. Microbial steroid transformations: current state and prospects. Appl Microbiol Biotechnol 2012, 94:1423-1447. 10.1007/s00253-012-4078-0, 22562163.
9. Donova MV. Transformation of steroids by actinobacteria: a review. Appl Biochem Microbiol 2007, 43:1-14.
10. Mahato SB, Garai S. Advances in microbial steroid biotransformation. Steroids 1997, 62:332-345. 10.1016/S0039-128X(96)00251-6, 9090793.
11. Agematu H, Matsumoto N, Fujii Y, Kabumoto H, Doi S, Machida K, Ishikawa J, Arisawa A. Hydroxylation of testosterone by bacterial cytochromes P450 using the Escherichia coli expression system. Biosci Biotech Biochem 2006, 70:307-311.
12. Ishikawa J, Yamashita A, Mikami Y, Hoshino Y, Kurita H, Hotta K, Shiba T, Hattori M. The complete genomic sequence of Nocardia farcinica IFM 10152. Proc Natl Acad Sci U S A 2004, 101:14925-14930. 10.1073/pnas.0406410101, 522048, 15466710.
13. Peterson JA, Lorence MC, Amarneh B. Putidaredoxin reductase and putidaredoxin. Cloning, sequence determination, and heterologous expression of the proteins. J Biol Chem 1990, 265:6066-6073.
14. Sabbadin F, Hyde R, Robin A, Hilgarth E-M, Delenne M, Flitsch S, Turner N, Grogan G, Bruce NC. LICRED: a versatile drop-in vector for rapid generation of redox-self-sufficient cytochrome P450s. ChemBioChem 2010, 11:987-994. 10.1002/cbic.201000104, 20425752.
15. Fragkaki AG, Angelis YS, Koupparis M, Tsantili-Kakoulidou A, Kokotos G, Georgakopoulos C. Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities: applied modifications in the steroidal structure. Steroids 2009, 74:172-197. 10.1016/j.steroids.2008.10.016, 19028512.
16. Schallmey A, den Besten G, Teune I, Kembaren R, Janssen D. Characterization of cytochrome P450 monooxygenase CYP154H1 from the thermophilic soil bacterium Thermobifida fusca. Appl Microbiol Biotechnol 2011, 89:1475-1485. 10.1007/s00253-010-2965-9, 3036808, 21057946.
17. Miroux B, Walker JE. Over-production of proteins in Escherichia coli: mutant hosts that allow synthesis of some membrane proteins and globular proteins at high levels. J Mol Biol 1996, 260:289-298. 10.1006/jmbi.1996.0399, 8757792.
18. Baldwin CVF, Woodley JM. On oxygen limitation in a whole cell biocatalytic Baeyer-Villiger oxidation process. Biotechnol Bioeng 2006, 95:362-369. 10.1002/bit.20869, 16862597.
19. Lisurek M, Kang M-J, Hartmann RW, Bernhardt R. Identification of monohydroxy progesterones produced by CYP106A2 using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry. Biochem Biophys Res Commun 2004, 319:677-82. 10.1016/j.bbrc.2004.05.037, 15178459.
20. Waxman DJ, Lapenson DP, Aoyama T, Gelboin HV, Gonzalez FJ, Korzekwa K. Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Arch Biochem Biophys 1991, 290:160-166. 10.1016/0003-9861(91)90602-F, 1898086.
21. Berrie JR, Williams RAD, Smith KE. Microbial transformations of steroids-XI. Progesterone transformation by Streptomyces roseochromogenes-purification and characterisation of the 16α-hydroxylase system. J Steroid Biochem 1999, 71:153-165.
22. Goetschel R, Bar R. Formation of mixed crystals in microbial conversion of sterols and steroids. Enzyme Microb Technol 1992, 14:462-469.
23. Arinbasarova AY, Koshcheyenko KA, Andrjushina VA, Grinenko GS, Skryabin GK. 1995, Russian: patent No. 1830949.
24. Uvardy N, Bartho I, Hantos G, Trinn M, Vida Z, Szejtli J, Stadler A, Habon I. 1985, UK: patent No. 2108965.
25. Fokina VV, Karpov AV, Sidorov IA, Andrjushina VA, Arinbasarova AY. The influence of β-cyclodextrin on the kinetics of 1-en-dehydrogenation of 6α-methylhydrocortisone by Arthrobacter globiformis cells. Appl Microbiol Biotechnol 1997, 47:645-649.
26. Druzhinina AV, Andryushina VA, Stytsenko TS, Voishvillo NE. Conversion of 17α-methyltestosterone to methandrostenolone by the bacterium Pimelobacter simplex VKPM Ac-1632 with the presence of cyclodextrins. Appl Biochem Microbiol 2008, 44:580-584.
27. Omura T, Sato R. The carbon monoxide-binding pigment of liver microsomes. Evidence for its hemoprotein nature. J Biol Chem 1964, 239:2370-2378.
28. Lacour T, Achstetter T, Dumas B. Characterization of recombinant adrenodoxin reductase homologue (Arh1p) from yeast implication in in vitro cytochrome P45011β monooxygenase system. J Biol Chem 1998, 273:23984-23992. 10.1074/jbc.273.37.23984, 9727014.