Radical mechanism of cyanophage phycoerythrobilin synthase (PebS)

Biochemical Journal

Volumn 433, Issue 3, 2011, Pages 469-476

  Busch, Andrea W U ^a   Reijerse, Edward J ^b   Lubitz, Wolfgang ^b   Hofmann, Eckhard ^a   Frankenberg Dinkel, Nicole ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

Bilin reductase; Cyanophage; EPR; Open chain tetrapyrrole; Phycoerythrobilin synthase; Radical

Indexed keywords

ASPARTIC ACID; BACTERIAL ENZYME; BILIVERDIN; BILIVERDIN IXALPHA; MUTANT PROTEIN; PHYCOERYTHROBILIN SYNTHASE; RADICAL; SYNTHETASE; UNCLASSIFIED DRUG;

ANAEROBIC METABOLISM; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYANOPHAGE; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STRUCTURE; ENZYME SUBSTRATE; ENZYME SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; REDUCTION; STEREOSPECIFICITY; WILD TYPE;

BACTERIOPHAGES; ELECTRON TRANSPORT; PHYCOBILINS; PHYCOERYTHRIN; VIRAL PROTEINS;

CYANOBACTERIA;

EID: 78751551667     PISSN: 02646021     EISSN: 14708728     Source Type: Journal    
DOI: 10.1042/BJ20101642     Document Type: Article

References (26)

1. Glazer, A. N. (1985) Light harvesting by phycobilisomes. Ann. Rev. Biophys. Biophys. Chem. 14, 47-77
2. Cornejo, J., Willows, R. D. and Beale, S. I. (1998) Phytobilin biosynthesis: cloning and expression of a gene encoding soluble ferredoxin-dependent heme oxygenase from Synechocystis sp. PCC 6803. Plant J. 15, 99-107
3. Frankenberg, N., Mukougawa, K., Kohchi, T. and Lagarias, J. C. (2001) Functional genomic analysis of the HY2 family of ferredoxin-dependent bilin reductases from oxygenic photosynthetic organisms. Plant Cell 13, 965-978
4. Frankenberg, N. and Lagarias, J. C. (2003) Phycocyanobilin:ferredoxin oxidoreductase of Anabaena sp. PCC 7120. Biochemical and spectroscopic. J. Biol. Chem. 278, 9219-9226
5. Tu, S. L., Gunn, A., Toney, M. D., Britt, R. D. and Lagarias, J. C. (2004) Biliverdin reduction by cyanobacterial phycocyanobilin:ferredoxin oxidoreductase (PcyA) proceeds via linear tetrapyrrole radical intermediates. J. Am. Chem. Soc. 126, 8682-8693
6. Dammeyer, T. and Frankenberg-Dinkel, N. (2008) Function and distribution of bilin biosynthesis enzymes in photosynthetic organisms. Photochem. Photobiol. Sci. 7, 1121-1130
7. Kohchi, T., Mukougawa, K., Frankenberg, N., Masuda, M., Yokota, A. and Lagarias, J. C. (2001) The ArabidopsisHY2 gene encodes phytochromobilin synthase, a ferredoxin-dependent biliverdin reductase. Plant Cell 13, 425-436
8. Dammeyer, T. and Frankenberg-Dinkel, N. (2006) Insights into phycoerythrobilin biosynthesis point toward metabolic channeling. J. Biol. Chem. 281, 27081-27089
9. Tu, S. L., Chen, H. C. and Ku, L. W. (2008) Mechanistic studies of the phytochromobilin synthase HY2 from Arabidopsis. J. Biol. Chem. 283, 27555-27564
10. Tu, S. L., Rockwell, N. C., Lagarias, J. C. and Fisher, A. J. (2007) Insight into the radical mechanism of phycocyanobilin-ferredoxin oxidoreductase (PcyA) revealed by X-ray crystallography and biochemical measurements. Biochemistry 46, 1484-1494
11. Sullivan, M. B., Coleman, M. L., Weigele, P., Rohwer, F. and Chisholm, S. W. (2005) Three Prochlorococcus cyanophage genomes: signature features and ecological interpretations. PLoS Biol. 3, e144
12. Dammeyer, T., Bagby, S. C., Sullivan, M. B., Chisholm, S. W. and Frankenberg-Dinkel, N. (2008) Efficient phage-mediated pigment biosynthesis in oceanic cyanobacteria. Curr. Biol. 18, 442-448
13. Dammeyer, T., Hofmann, E. and Frankenberg-Dinkel, N. (2008) Phycoerythrobilin synthase (PebS) of a marine virus: crystal structures of the biliverdin complex and the substrate-free form. J. Biol. Chem. 283, 27547-27554
14. Kabsch, W. (1993) Automatic processing of rotation diffraction data from crystals of initially unknown symmetry and cell constants. J. Appl. Crystallogr. 26, 795-800
15. Emsley, P. and Cowtan, K. (2004) Coot: model-building tools for molecular graphics. Acta Crystallogr. Sect. D Biol. Crystallogr. 60, 2126-2132
16. Murshudov, G. N., Vagin, A. A. and Dodson, E. J. (1997) Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr. Sect. D Biol. Crystallogr. 53, 240-255
17. Adams, P. D., Grosse-Kunstleve, R. W., Hung, L.-W., Ioerger, T. R., McCoy, A. J., Moriarty, N. W., Read, R. J., Sacchettini, J. C., Sauter, N. K. and Terwilliger, T. C. (2002) PHENIX: building new software for automated crystallographic structure determination. Acta Crystallogr. Sect. D Biol. Crystallogr. 58, 1948-1954
18. Sullivan, M. B., Huang, K. H., Ignacio-Espinoza, J. C., Berlin, A. M., Kelly, L., Weigele, P. R., Defrancesco, A. S., Kern, S. E., Thompson, L. R., Young, S. et al. (2010) Genomic analysis of oceanic cyanobacterial myoviruses compared with T4-like myoviruses from diverse hosts and environments. Environ. Microbiol. 12, 3035-3056
19. Gossauer, A. and Weller, J. P. (1978) Synthesis of bile pigments. 9. Chemical total synthesis of (+)-(2R,16R)- and (+)-(2S,16R)-phycoerythrobilin dimethyl ester. J. Am. Chem. Soc. 100, 5928-5933
20. Beale, S. I. and Cornejo, J. (1984) Enzymic transformation of biliverdin to phycocyanobilin by extracts of the unicellular red alga Cyanidium caldarium. Plant Physiol. 76, 7-15
21. Beale, S. I. and Cornejo, J. (1991) Biosynthesis of phycobilins. 3(Z)-Phycoerythrobilin and 3(Z)-phycocyanobilin are intermediates in the formation of 3(E)-phycocyanobilin from biliverdin IXa. J. Biol. Chem. 266, 22333-22340
22. McDowell, M. T. and Lagarias, J. C. (2001) Purification and biochemical properties of phytochromobilin synthase from etiolated oat seedlings. Plant Physiol. 126, 1546-1554
23. Tu, S. L., Sughrue, W., Britt, R. D. and Lagarias, J. C. (2006) A conserved histidine-aspartate pair is required for exovinyl reduction of biliverdin by a cyanobacterial phycocyanobilin:ferredoxin oxidoreductase. J. Biol. Chem. 281, 3127-3136
24. Hagiwara, Y., Sugishima, M., Takahashi, Y. and Fukuyama, K. (2006) Crystal structure of phycocyanobilin:ferredoxin oxidoreductase in complex with biliverdin IXa, a key enzyme in the biosynthesis of phycocyanobilin. Proc. Natl. Acad. Sci. U.S.A. 103, 27-32
25. Dammeyer, T., Michaelsen, K. and Frankenberg-Dinkel, N. (2007) Biosynthesis of open-chain tetrapyrroles in Prochlorococcus marinus. FEMS Microbiol. Lett. 271, 251-257
26. Stoll, S., Gunn, A., Brynda, M., Sughrue, W., Kohler, A. C., Ozarowski, A., Fisher, A. J., Lagarias, J. C. and Britt, R. D. (2009) Structure of the biliverdin radical intermediate in phycocyanobilin:ferredoxin oxidoreductase identified by high-field EPR and DFT. J. Am. Chem. Soc. 131, 1986-1995