Toward a mechanism for biliprotein lyases: Revisiting nucleophilic addition to phycocyanobilin

Journal of the American Chemical Society

Volumn 131, Issue 15, 2009, Pages 5399-5401

  Tu, Jun Ming ^a,b,c   Zhou, Ming ^a   Haessner, Rainer ^d   Plöscher, Matthias ^c   Eichacker, Lutz ^c   Scheer, Hugo ^c   Zhao, Kai Hong ^a,b  

^a HUAZHONG AGRICULTURAL UNIVERSITY   (China)

^b HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c UNIVERSITY OF MUNICH   (Germany)

^d TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

APOPROTEINS; BACK-ISOMERIZATION; DIRECT TRANSFER; LIGHT-HARVESTING COMPLEX; NUCLEOPHILIC ADDITIONS; PHYCOBILIPROTEINS; PHYCOBILISOMES; PHYCOVIOLOBILIN; REACTION MECHANISM;

ADDITION REACTIONS;

ENZYMES;

HISTIDINE; LYASE; NUCLEOPHILE; PHYCOBILIPROTEIN; PHYCOCYANOBILIN; PHYTOCHROME; UNCLASSIFIED DRUG; APOPROTEIN; IMIDAZOLE; IMIDAZOLE DERIVATIVE; PHYCOBILIN; PHYCOCYANIN; THIOL DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHROMATOPHORE; ISOMERIZATION; PROTEIN BINDING; PROTEIN STRUCTURE; REACTION ANALYSIS; BIOMIMETICS; CHEMISTRY; LIGHT HARVESTING SYSTEM; METABOLISM; SYNTHESIS;

APOPROTEINS; BIOMIMETICS; IMIDAZOLES; LIGHT-HARVESTING PROTEIN COMPLEXES; LYASES; PHYCOBILINS; PHYCOBILIPROTEINS; PHYCOCYANIN; SULFHYDRYL COMPOUNDS;

EID: 67849128768     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9002348     Document Type: Article

References (39)

1. Scheer, H. In Light Reaction Path of Photosynthesis; Fong, F. K., Ed.; Springer: Berlin, 1982; p 7.
2. (b) Sidler, W. A. In The Molecular Biology of Cyanobacteria; Bryant, D. A., Ed.; Kluwer: Dordrecht, The Netherlands, 1994; p 139.
3. (a) Schmidt, U.; Westphal, H.; Worm, K.; Braslavsky, S. E.; Gartner, W.; Schaffner, K. J. Photochem. Photobiol., B 1996, 34, 73-77.
4. (b) Inomata, K.; Noack, S.; Hammam, M. A.; Khawn, H.; Kinoshita, H.; Murata, Y.; Michael, N.; Scheerer, P.; Krauss, N.; Lamparter, T. J. Biol. Chem. 2006, 281, 28162-28173.
5. (c) Hanzawa, H.; Shinomura, T.; Inomata, K.; Kakiuchi, T.; Kinoshita, H.; Wada, K.; Furuya, M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4725-4729.
6. (d) Lindner, I.; Braslavsky, S. E.; Schaffner, K.; Gärtner, W Angew. Chem., Int. Ed.. 2000, 39, 3269-3271
7. (a) Scheer, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 230-250.
8. (b) Braslavsky, S. E.; Holzwarth, A. R.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1983, 22, 656-674.
9. (c) Scheer, H. in Light-Harvesting Antennas in Photosynthesis; Green, B., ParsonW., Eds.; Kluwer: Dordrecht, The Netherlands, 2003; p 29.
10. (a) Wu, S.-H.; Lagarias, J. C. Biochemistry 2000, 39, 13487-13495.
11. (b) Zhao, K.-H.; Ran, Y.; Li, M.; Sun, Y.-N.; Zhou, M.; Storf, M.; Kupka, M.; Böhm, S.; Bubenzer, C.; Scheer, H. Biochemistry 2004, 43, 11576-11588.
12. 6d This situation is reminiscent of the c-type cytochromes. See: Daltrop, O.; Allen, J. W.; Willis, A. C.; Ferguson, S. J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7872-7876.
13. (a) Fairchild, C. D.; Glazer, A. N. J. Biol. Chem. 1994, 269, 8686-8694.
14. (b) Shen, G.; Schluchter, W. M.; Bryant, D. A. J. Biol. Chem. 2008, 283, 7503-7512.
15. (c) Shen, G.; Saunee, N. A.; Williams, S. R.; Gallo, E. F.; Schluchter, W. M.; Bryant, D. A. J. Biol. Chem. 2006, 281, 17768-17778.
16. (d) Scheer, H.; Zhao, K.-H. Mol. Microbiol. 2008, 68, 263-276.
17. (e) Zhao, K.-H.; Su, P.; Tu, J. M.; Wang, X.; Liu, H.; Ploscher, M.; Eichacker, L.; Yang, B.; Zhou, M.; Scheer, H. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 14300-14305.
18. (f) Zhao, K.-H.; Su, P.; Li, J.; Tu, J. M.; Zhou, M.; Bubenzer, C.; Scheer, H. J. Biol. Chem. 2006, 281, 8573-8581.
19. 1-nucleophile adducts) and distinguished by the positions of hydrogens in the tetrapyrrole system (see Scheme 1).
20. (a) Storf, M.; Parbel, A.; Meyer, M.; Strohmann, B.; Scheer, H.; Deng, M.; Zheng, M.; Zhou, M.; Zhao, K.-H. Biochemistry 2001, 40, 12444.
21. (b) Blot, N.; Wu, X.-J.; Thomas, J.-C.; Zhang, J.; Garczarek, L.; Böhm, S.; Tu, J.-M.; Zhou, M.; Plöscher, M.; Eichacker, L.; Partensky, F.; Scheer, H.; Zhao, K.-H. J. Biol. Chem. [Online early access]. DOI: 10.1074/ jbc.M809784200. Published Online: Jan 31, 2009.
22. (a) Schluchter, W. M.; Bryant, D. A. In Heme, Chlorophyll, and Bilins; Smith, A. G., Witty, M., Eds.; Humana Press: Totowa, NJ, 2002; p 311.
23. (b) Böhm, S.; Endres, S.; Scheer, H.; Zhao, K.-H. J. Biol. Chem. 2007, 282, 25357-25366.
24. Tu, J.-M.; Kupka, M.; Böhm, S.; Plöscher, M.; Eichacker, L.; Zhao, K.-H.; Scheer, H. Photosynth. Res. 2008, 95, 163-168.
25. (a) Lagarias, J. C.; Klotz, A. V.; Dallas, J. L.; Glazer, A. N.; Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Biol. Chem. 1988, 263, 12977-12985.
26. (b) Bishop, J. E.; Rapoport, H.; Klotz, A. V.; Chan, C. F.; Glazer, A. N.; Füglistaller, P.; Zuber, H. J. Am. Chem. Soc. 1987, 109, 875-881.
27. Stumpe, H.; Mueller, N.; Grubmayr, K. Tetrahedron Lett. 1993, 34, 4165-4168.
28. 16 These addition products can also yield chromophore 3 by vinylogous substitution. No spectral evidence for such intermediates has been found, but the absorptions may be buried under those of 3 and 5.
29. (a) Manitto, P.; Monti, D. Experientia 1979, 35, 1418-1420.
30. (b) Kufer, W.; Scheer, H. Hoppe-Seyler's Z. Physiol. Chem. 1979, 360, 935-956.
31. (c) Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer: Vienna, 1989.
32. Zhao, K.-H.; Zhu, J.; Song, B.; Zhou, M.; Storf, M.; Bohm, S.; Bubenzer, C.; Scheer, H. Biochim. Biophys. Acta 2004, 1657, 131-145.
33. (a) Caballol, R.; Ribó, J. M.; Trull, F. R.; Vallès, A. Monatsh. Chem. 1987, 118, 1011-1029.
34. (b) Falk, H.; Gsaller, H.; Hubauer, E.; Mueller, N Monatsh. Chem. 1985, 116, 939-959.
35. Köst-Reyes, E.; Köst, H.-P. Eur. J. Biochem. 1979, 102, 83-91.
36. Ikeuchi, M.; Ishizuka, T. Photochem. Photobiol. Sci. 2008, 7, 1159-1167.
37. Zhao, K.-H.; Haessner, R.; Cmiel, E.; Scheer, H. Biochim. Biophys. Acta 1995, 1228, 235-248.
38. (a) Tu, S. L.; Rockwell, N. C.; Lagarias, J. C.; Fisher, A. J. Biochemistry 2007, 46, 1484-1494.
39. (b) Dammeyer, T.; Frankenberg-Dinkel, N. Photochem. Photobiol. Sci. 2008, 7, 1121-1130.