Regioselective hydroxylation of norisoprenoids by CYP109D1 from Sorangium cellulosum so ce56

Applied Microbiology and Biotechnology

Volumn 88, Issue 2, 2010, Pages 485-495

  Khatri, Yogan ^a   Girhard, Marco ^b   Romankiewicz, Anna ^c   Ringle, Michael ^a   Hannemann, Frank ^a   Urlacher, Vlada B ^b   Hutter, Michael C ^a   Bernhardt, Rita ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

^c UNIVERSITY OF STUTTGART   (Germany)

Author keywords

CYP109D1; Cytochromes P450; Norisoprenoids; Sorangium cellulosum So ce56; Terpenoids

Indexed keywords

CYP109D1; CYTOCHROMES P450; NORISOPRENOIDS; SORANGIUM; TERPENOIDS;

BIOCATALYSTS; DRUG PRODUCTS; LIPIDS; ODORS; OLEFINS; REACTION KINETICS; REGIOSELECTIVITY;

HYDROXYLATION;

ALPHA IONONE; BETA IONONE; CYP109D1; CYTOCHROME; NORISOPRENOID; UNCLASSIFIED DRUG;

ALCOHOL; BACTERIUM; CATALYST; CYTOCHROME; NUCLEAR MAGNETIC RESONANCE; OXIDATION; TERPENE;

AROMA; ARTICLE; BIOCATALYST; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HYDROXYLATION; MYXOCOCCALES; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTON NUCLEAR MAGNETIC RESONANCE; REGIOSELECTIVITY; SORANGIUM CELLULOSUM;

BACTERIAL PROTEINS; CYTOCHROME P-450 ENZYME SYSTEM; HYDROXYLATION; MODELS, MOLECULAR; MYXOCOCCALES; NORISOPRENOIDS;

POLYANGIUM CELLULOSUM;

EID: 77956225590     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-2756-3     Document Type: Article

References (57)

1. D Appel S Lutz-Wahl P Fischer U Schwaneberg RD Schmid 2001 A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes J Biotechnol 88 167 171 10.1016/S0168-1656(01)00249-8
2. K Arnold L Bordoli J Kopp T Schwede 2006 The SWISS-MODEL Workspace: a web-based environment for protein structure homology modeling Bioinformatics 22 195 201 10.1093/bioinformatics/bti770
3. SG Bell A Dale NH Rees LL Wong 2010 A cytochrome P450 class I electron transfer system from Novosphingobium aromaticivorans Appl Microbiol Biotechnol 86 163 175 10.1007/s00253-009-2234-y
4. R Bernhardt 2006 Cytochromes P450 as versatile biocatalysts J Biotechnol 124 128 145 10.1016/j.jbiotec.2006.01.026
5. Brenna E, Fuganti C, Serra S, Kraft P (2002) Optically active ionones and derivatives: Preparation and olfactory properties. Eur J Org Chem 967-978
6. R Buchecker R Egli H Regel-Wild C Tscharner CH Eugster G Uhde G Ohloff 1973 Absolute konfiguration der enantiomeren α-cyclogeraniumsäuren, α-cyclogeraniale, α-ionone, γ-ionone, α- und ε-Carotine Helv Chim Acta 56 2548 2563 10.1002/hlca.19730560739
7. B Buehler A Schmid 2004 Process implementation aspects for biocatalytic hydrocarbon oxyfunctionalization J Biotechnol 113 183 210 10.1016/j.jbiotec. 2004.03.027
8. AB Carmichael LL Wong 2001 Protein engineering of Bacillus megaterium CYP102: the oxidation of polycyclic aromatic hydrocarbons Eur J Biochem 268 3117 3125 10.1046/j.1432-1327.2001.02212.x
9. A Celik SL Flitsch NJ Turner 2005 Efficient terpene hydroxylation catalysts based upon P450 enzymes derived from actinomycetes Org Biomol Chem 3 2930 2934 10.1039/b506159h
10. MI Colombo J Zinczuk EA Ruveda 1992 Synthetic routes to forskolin Tetrahedron 48 963 1037 10.1016/S0040-4020(01)88199-0
11. CC de Carvalho MM da Fonseca 2006 Biotransformation of terpenes Biotechnol Adv 24 134 142 10.1016/j.biotechadv.2005.08.004
12. WA Duetz JB van Beilen B Witholt 2001 Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis Curr Opin Biotechnol 12 419 425 10.1016/S0958-1669(00) 00237-8
13. WA Duetz H Bouwmeester JB van Beilen B Witholt 2003 Biotransformation of limonene by bacteria, fungi, yeast, and plants Appl Microbiol Biotechnol 61 269 277
14. W Eschenmoser P Uevelhart CH Eugster 1981 Synthesis and structure of the enantiomeric 6-hydroxy-α-ionone and cis- and trans-5, 6-dihydroxy-5, 6-dihydro-β-ionone Helv Chim Acta 64 2681 2690 10.1002/hlca.19810640826
15. KM Ewen F Hannemann Y Khatri O Perlova R Kappl D Krug J Hüttermann R Müller R Bernhardt 2009 Genome mining in Sorangium cellulosum So ce56: identification and characterization of the homologous electron transfer proteins of a myxobacterial cytochrome P450 J Biol Chem 284 28590 28598 10.1074/jbc.M109.021717
16. M Girhard K Machida M Itoh RD Schmid A Arisawa VB Urlacher 2009 Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system Microb Cell Fact 8 36 10.1186/1475-2859-8-36
17. M Girhard T Klaus Y Khatri R Bernhardt VB Urlacher 2010 Characterization of the versatile monooxygenase CYP109B1 from Bacillus subtilis Appl Microbiol Biotechnol 87 595 607 10.1007/s00253-010-2472-z 10.1007/s00253-010-2472-z
18. N Guex MC Peitsch 1997 SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modelling Electrophoresis 18 2714 2723 10.1002/elps.1150181505
19. A Haag W Eschenmoser CH Eugster 1980 Synthese von (-)-(R)-4-hydroxy- β-ionone and (-)-(5R, 6S)-5-Hydroxy-4, 5-dihydro-α-ionone aus (-)-(S)-α-ionone Helv Chim Acta 63 10 15 10.1002/hlca.19800630103
20. F Hannemann C Virus R Bernhardt 2006 Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases J Biotechnol 124 172 181 10.1016/j.jbiotec.2006.01.009
21. F Hannemann A Bichet KM Ewen R Bernhardt 2007 Cytochrome P450 systems-biological variations of electron transport chains Biochim Biophys Acta 1770 330 344
22. R Huey GM Morris AJ Olson DS Goodsell 2007 A semiempirical free energy force field with charge-based desolvation J Comput Chem 28 1145 1152 10.1002/jcc.20634
23. T Ishida H Enomoto R Nishida 2008 New attractants for males of the solanaceous fruit fly Bactrocera latifrons J Chem Ecol 34 1532 1535 10.1007/s10886-008-9562-8
24. H Kakeya T Sugi H Ohta 1991 Biochemical preparation of optically active 4-hydroxy-β-ionone and its transformation of (S)-6-hydroxy-α-ionone Agric Biol Chem 55 1873 1876
25. E Kovats 1958 Gas-chromatographische Charakterisierung organischer Verbindungen. Teil 1: Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone Helv Chim Acta 41 1915 1932 10.1002/hlca.19580410703
26. MA Larkin G Blackshields NP Brown R Chenna PA McGettigan H McWilliam F Valentin IM Wallace A Wilm R Lopez JD Thompson TJ Gibson DG Higgins 2007 CLUSTALW, version 2 Bioinformatics 23 2947 2948 10.1093/bioinformatics/btm404
27. C Larroche C Creuly JB Gros 1995 Fed-batch biotransformation of β-ionone by Aspergillus niger Appl Microbiol Biotechnol 43 222 227 10.1007/BF00172816
28. M Lisurek B Simgen I Antes R Bernhardt 2008 Theoretical and experimental evaluation of a CYP106A2 low homology model and production of mutants with changed activity and selectivity of hydroxylation Chembiochem 9 1439 1449 10.1002/cbic.200700670
29. S Lochynski K Kowalska C Wawrzenczyk 2002 Synthesis and odour characteristics of new derivatives from the carane system Flavour Frag J 3 181 186 10.1002/ffj.1078
30. S Lutz-Wahl P Fischer C Schmidt-Dannert W Wohlleben B Hauer RD Schmid 1998 Stereo- and regioselective hydroxylation of alpha-Ionone by Streptomyces Strains Appl Environ Microbiol 64 3878 3881
31. McCudry H (1989) Fruiting gliding bacteria. In: Holt J (ed) Bergey's manual of systematic bacteriology. Williams & Wilkins, Baltimore, pp 2139-2143
32. KJ McLean P Carroll DG Lewis AJ Dunford HE Seward R Neeli MR Cheesman L Marsollier P Douglas WE Smith I Rosenkrands ST Cole D Leys T Parish AW Munro 2008 Characterization of active site structure in CYP121. A cytochrome P450 essential for viability of Mycobacterium tuberculosis H37Rv J Biol Chem 283 33406 33416 10.1074/jbc.M802115200
33. D Menche F Arikan O Perlova N Horstmann W Ahlbrecht SC Wenzel R Jansen H Irschik R Müllar 2008 Stereochemical determination and complex biosynthetic assembly of ethangien, a highly potent RNA-polymerase inhibitor from the myxobacterium Sorangium cellulosum J Am Chem Soc 130 14234 14243 10.1021/ja804194c
34. Y Mikami Y Fukunaga M Arita T Kisaki 1981 Microbial transformation of β-ionone and β-methylionone Appl Environ Microbiol 41 610 617
35. GM Morris DS Goodsell RS Halliday R Huey WE Hart RK Belew AJ Olson 1998 Automated docking using a lamarckian genetic algorithm and empirical binding free energy function J Comput Chem 19 1639 1662 10.1002/(SICI)1096- 987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
36. K Nishihara M Kanemori M Kitagawa H Yanagi T Yura 1998 Chaperone Coexpression Plasmids:Differential and synergistic roles of DnaK-DnaJ-GrpE and GroEL-GroES in assisting folding of an allergen of Japanese cedar pollen, Cryj2, in Escherichia coli Appl Environ Microbiol 64 1694 1699
37. T Omura R Sato 1964 The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature J Biol Chem 239 2370 2378
38. O Perlova K Gerth O Kaiser A Hans R Müller 2006 Identification and analysis of the chivosazol biosynthetic gene cluster from the myxobacterial model strain Sorangium cellulosum So ce56 J Biotechnol 121 174 191 10.1016/j.jbiotec.2005.10.011
39. Pybus DH, Sell CS (1999) The chemistry of fragrances. The Royal Society of Chemistry, London
40. Reichenbach H (2004) The Myxococcales. In: Garrity GM (ed) Bergey's manual of systematic bacteriology. Springer, New York, pp 1059-1143
41. SC Roberts 2007 Production and engineering of terpenoids in plant cell culture Nat Chem Biol 3 387 395 10.1038/nchembio.2007.8
42. Y Sagara A Wada Y Takata MR Waterman K Sekimizu T Horiuchi 1993 Direct expression of adrenodoxin reductase in Escherichia coli and the functional characterization Biol Pharm Bull 16 627 630
43. MF Sanner 1999 Python: a programming language for software integration and development J Mol Graph Model 17 57 61
44. S Schneiker O Perlova O Kaiser K Gerth A Alici MO Altmeyer D Bartels T Bekel S Beyer E Bode HB Bode CJ Bolten, et al. 2007 Complete genome sequence of the myxobacterium Sorangium cellulosum Nat Biotech 25 1281 1289 10.1038/nbt1354
45. T Schwede J Kopp N Guex MC Peitsch 2003 SWISS-MODEL: an automated protein homology-modeling server Nucleic Acids Res 31 3381 3385 10.1093/nar/gkg520
46. L Stanislaw K Kowaiska C Wawrzwnczyk 2002 Synthesis and odour characteristics of new derivatives from the carane system Flavour Frag J 17 181 186 10.1002/ffj.1078
47. H Uhlmann R Kraft R Bernhardt 1994 C-terminal region of adrenodoxin affects its structural integrity and determines differences in its electron transfer function to cytochrome P-450 J Biol Chem 269 22557 22564
48. VB Urlacher RD Schmid 2002 Biotransformations using prokaryotic P450 monooxygenases Curr Opin Biotechnol 13 557 564 10.1016/S0958-1669(02)00357-9
49. VB Urlacher A Makhsumkhanov RD Schmid 2006 Biotransformation of beta-ionone by engineered cytochrome P450 BM-3 Appl Microbiol Biotechnol 70 53 59 10.1007/s00253-005-0028-4
50. C Virus R Bernhardt 2008 Molecular evolution of a steroid hydroxylating cytochrome P450 using a versatile steroid detection system for screening Lipids 43 1133 1141 10.1007/s11745-008-3236-8
51. SC Wenzel R Müller 2007 Myxobacterial natural product assembly lines: fascinating examples of curious biochemistry Nat Prod Rep 24 1211 1224 10.1039/b706416k
52. SC Wenzel R Müller 2009 Myxobacteria-'microbial factories' for the production of bioactive secondary metabolites Mol Biosyst 5 567 574 10.1039/b901287g
53. JW Williams JF Morrison 1979 The kinetics of reversible tight-binding inhibition Methods Enzymol 63 437 467 10.1016/0076-6879(79)63019-7
54. Winterhalter P, Rouseff RL (2002) Carotenoid-derived aroma compounds. Am Chem Soc, Washington
55. ST Withers JD Keasling 2007 Biosynthesis and engineering of isoprenoid small molecules Appl Microbiol Biotechnol 73 980 990 10.1007/s00253-006-0593-1
56. Y Yamazaki Y Hayashi M Arita T Hieda Y Mikami 1988 Microbial conversion of α-ionone, α-methylionone, and α-isomethylionone Appl Environ Microbiol 54 2354 2360
57. A Zöllner N Kagawa MR Waterman Y Nonaka K Takio Y Shiro F Hannemann R Bernhardt 2008 Purification and functional characterization of human 11-beta hydroxylase expressed in Escherichia coli FEBS J 275 799 810 10.1111/j.1742-4658.2008.06253.x