Photosystem I from plants as a bacterial cytochrome P450 surrogate electron donor: Terminal hydroxylation of branched hydrocarbon chains

Biotechnology Letters

Volumn 34, Issue 2, 2012, Pages 239-245

  Jensen, Kenneth ^a   Johnston, Jonathan B ^b   de Montellano, Paul R Ortiz ^b   Møller, Birger Lindberg ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

hydroxylation; Cytochrome P450; Light driven biosynthesis; Lipid hydroxyllase; Photosystem I

Indexed keywords

BIOTECHNOLOGY APPLICATIONS; BRANCHED HYDROCARBONS; CHEMICAL SYNTHESIS; COFACTORS; COMMERCIAL POTENTIAL; CYTOCHROME P450; ELECTRON CARRIER; ELECTRON DONORS; ELECTRON FLOW; MYCOBACTERIUM TUBERCULOSIS; NAD(P)H; OXIDOREDUCTASES; PHOTO-REDUCTION; PHOTOSYSTEM I; STEREOSPECIFIC;

BIOCHEMISTRY; HYDROCARBONS; HYDROXYLATION; IODINE; SYNTHESIS (CHEMICAL);

ELECTRONS;

CYTOCHROME P450; HYDROCARBON; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; ENZYMOLOGY; GENETICS; HYDROXYLATION; METABOLISM; MYCOBACTERIUM TUBERCULOSIS; PHOTOSYSTEM I; SUNLIGHT;

CYTOCHROME P-450 ENZYME SYSTEM; HYDROCARBONS; HYDROXYLATION; MYCOBACTERIUM TUBERCULOSIS; NADP; PHOTOSYSTEM I PROTEIN COMPLEX; SUNLIGHT;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS;

EID: 84856217991     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-011-0768-4     Document Type: Article

References (28)

1. Asada K (1999) The water-water cycle in chloroplasts: scavenging of active oxygens and dissipation of excess photons. Annu Rev Plant Physiol Plant Mol Biol 50: 601-639.
2. Cirino PC, Arnold FH (2003) A self-sufficient peroxide-driven hydroxylation biocatalyst. Angew Chem Int Edit 42: 3299-3301.
3. Denisov IG, Makris TM, Sligar SG, Schlichting I (2005) Structure and chemistry of cytochrome P450. Chem Rev 105: 2253-2277.
4. Furbank RT, Badger MR (1983) Oxygen exchange associated with electron transport and photophosphorylation in spinach thylakoids. Biochim Biophys Acta Bioenerg 723: 400-409.
5. Goni G, Zollner A, Lisurek M, Velazquez-Campoy A, Pinto S, Gomez-Moreno C, Hannemann F, Bernhardt R, Medina M (2009) Cyanobacterial electron carrier proteins as electron donors to CYP106A2 from Bacillus megaterium ATCC 13368. Biochim Biophys Acta 1794: 1635-1642.
6. Ham MH, Choi JH, Boghossian AA, Jeng ES, Graff RA, Heller DA, Chang AC, Mattis A, Bayburt TH, Grinkova YV, Zeiger AS, van Vliet KJ, Hobbie EK, Sligar SG, Wraight CA, Strano MS (2010) Photoelectrochemical complexes for solar energy conversion that chemically and autonomously regenerate. Nat Chem 2: 929-936.
7. Hannemann F, Bichet A, Ewen KM, Bernhardt R (2007) Cytochrome P450 systems-biological variations of electron transport chains. Biochim Biophys Acta 1770: 330-344.
8. Hollmann F, Witholt B, Schmid A (2002) [Cp*Rh(bpy)(H2O)](2+): a versatile tool for efficient and non-enzymatic regeneration of nicotinamide and flavin coenzymes. J Mol Catal B Enzym 19: 167-176.
9. Jensen K, Møller BL (2010) Plant NADPH-cytochrome P450 oxidoreductases. Phytochemistry 71: 132-141.
10. Jensen K, Jensen PE, Møller BL (2011) Light-driven cytochrome P450 hydroxylations. ACS Chem Biol 6: 533-539.
11. Johnston JB, Kells PM, Podust LM, Ortiz de Montellano PR (2009) Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis. Proc Natl Acad Sci USA 106: 20687-20692.
12. Johnston JB, Ouellet H, Ortiz de Montellano PR (2010) Functional redundancy of steroid C26-monooxygenase activity in Mycobacterium tuberculosis revealed by biochemical and genetic analyses. J Biol Chem 285: 36352-36360.
13. Joo H, Lin Z, Arnold FH (1999) Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature 399: 670-673.
14. Krishnan S, Wasalathanthri D, Zhao LL, Schenkman JB, Rusling JF (2011) Efficient bioelectronic actuation of the natural catalytic pathway of human metabolic cytochrome P450s. J Am Chem Soc 133: 1459-1465.
15. Loughlin WA (2000) Biotransformations in organic synthesis. Bioresource Technol 74: 49-62.
16. Medina M, Hervas M, Navarro JA, De la Rosa MA, Gomez-Moreno C, Tollin G (1992) A laser flash absorption spectroscopy study of Anabaena sp. PCC 7119 flavodoxin photoreduction by photosystem I particles from spinach. FEBS Lett 313: 239-242.
17. Nath A, Atkins WM, Sligar SG (2007) Applications of phospholipid bilayer nanodiscs in the study of membranes and membrane proteins. Biochemistry 46: 2059-2069.
18. Naver H, Scott MP, Golbeck JH, Møller BL, Scheller HV (1996) Reconstitution of barley photosystem I with modified PSI-C allows identification of domains interacting with PSI-D and PSI-A/B. J Biol Chem 271: 8996-9001.
19. Ouellet H, Johnston JB, de Ortiz Montellano PR (2010) The Mycobacterium tuberculosis cytochrome P450 system. Arch Biochem Biophys 493: 82-95.
20. Powles SB (1984) Photoinhibition of photosynthesis induced by visible-light. Annu Rev Plant Phys 35: 15-44.
21. Reipa V, Mayhew MP, Vilker VL (1997) A direct electrode-driven P450 cycle for biocatalysis. Proc Natl Acad Sci USA 94: 13554-13558.
22. Scheller HV, Svendsen I, Møller BL (1989) Subunit composition of photosystem I and identification of center X as a [4Fe-4S] iron-sulfur cluster. J Biol Chem 264: 6929-6934.
23. Sono M, Roach MP, Coulter ED, Dawson JH (1996) Heme-containing oxygenases. Chem Rev 96: 2841-2888.
24. Tishkov VI, Galkin AG, Fedorchuk VV, Savitsky PA, Rojkova AM, Gieren H, Kula MR (1999) Pilot scale production and isolation of recombinant NAD+- and NADP+-specific formate dehydrogenases. Biotechnol Bioeng 64: 187-193.
25. Tjus SE, Scheller HV, Andersson B, Møller BL (2001) Active oxygen produced during selective excitation of photosystem I is damaging not only to photosystem I, but also to photosystem II. Plant Physiol 125: 2007-2015.
26. Udit AK, Hill MG, Gray HB (2006) Electrochemistry of cytochrome P450BM3 in sodium dodecyl sulfate films. Langmuir 22: 10854-10857.
27. van der Donk WA, Zhao H (2003) Recent developments in pyridine nucleotide regeneration. Curr Opin Biotechnol 14: 421-426.
28. Wirtz M, Klucik J, Rivera M (2000) Ferredoxin-mediated electrocatalytic dehalogenation of haloalkanes by cytochrome P450(cam). J Am Chem Soc 122: 1047-1056.