On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond

Chemistry - A European Journal

Volumn 7, Issue 19, 2001, Pages 4198-4204

  Fujimoto, Yukari ^a   Ishihara, Jun ^a,b   Maki, Shojiro ^a,c   Fujioka, Naoko ^a   Wang, Tao ^a   Furuta, Takumi ^a   Fishkin, Nathan ^a   Borhan, Babak ^a,d   Berova, Nina ^a   Nakanishi, Koji ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b HOKKAIDO UNIVERSITY   (Japan)

^c UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

^d MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Chirality; Circular dichroism; Conformation analysis; Receptors; Retinal; Rhodopsin

Indexed keywords

CONFORMATIONS; ISOMERIZATION; PIGMENTS; PROTEINS;

INCUBATIONS;

CHROMOPHORES;

GUANINE NUCLEOTIDE BINDING PROTEIN; OPSIN; RETINAL; RHODOPSIN;

ANIMAL; ARTICLE; CATTLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CHEMISTRY; CHROMATOPHORE; CIRCULAR DICHROISM; CROSS LINKING; ISOMER; ISOMERISM; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; STEREOISOMERISM; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; CATTLE; CIRCULAR DICHROISM; MODELS, MOLECULAR; OPSIN; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; RETINALDEHYDE; RHODOPSIN; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 0035476603     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011001)7:19<4198::AID-CHEM4198>3.0.CO;2-X     Document Type: Article

References (49)

1. M. Ottolenghi, M. Sheves, Isr. J. Chem. 1995, 35, 193.
2. T. Gudermann, B. Nurnberg, G. Schultz, J. Mol. Med. 1995, 73, 51.
3. T. P. Sakmar, Prog. Nucleic Acid Res. Mol. Biol. 1998, 59, 1.
4. K. Palczewski in Methods in Enzymology, Vol. 316: Vertebrate Phototransduction and the Visual Cycle, Part A (Ed.: K. Palczewski), Academic Press, 2000.
5. P. A. Hargrave, Invest. Opthamol. Visual Sci. 2001, 42, 3.
6. K. Palczewski, T. Kumasaka, T. Hori, C. A. Behnke, H. Motoshima, B. A. Fox, I. Le Trong, D. C. Teller, T. Okada, R. E. Stenkamp, M. Yamamoto, M. Miyano, Science 2000, 289, 739.
7. T. Okada, I. Le Trong, B. A. Fox, C. A. Behnke, R. E. Stenkamp, K. Palczewski, J. Struct. Biol. 2000, 130, 73.
8. D. Bownds, Nature 1967, 216, 1178.
9. T. P. Sakmar, R. R. Franke, H. G. Khorana, Proc. Natl. Acad. Sci. USA 1989, 86, 8309.
10. J. Nathans, Biochemistry 1990, 29, 9746.
11. K. Nakanishi, Am. Zool. 1991, 31, 479.
12. K. Nakanishi, Pure Appl. Chem. 1991, 63, 161.
13. B. Honig, U. Dinur, K. Nakanishi, N. V. Balogh, M. A. Gawinowicz, M. Arnaboldi, M. G. Motto, J. Am. Chem. Soc. 1979, 101, 7084.
14. B. Konig, A. Arendt, J. H. McDowell, M. Kahlert, P. A. Hargrave, K. P. Hofmann, Proc. Natl. Acad. Sci. USA 1989, 86, 6878.
15. L. Stryer, J. Biol. Chem. 1991, 266, 10 711.
16. P. A. Hargrave, J. H. McDowell, FASEB J. 1992, 6, 2323.
17. H. G. Khorana, J. Biol. Chem. 1992, 267, 1.
18. J. Nathans, Biochemistry 1992, 31, 4923.
19. K. P. Hofmann, S. Jager, O. P. Ernst, Isr. J. Chem. 1995, 35, 339.
20. C. K. Meyer, M. Bohme, A. Ockenfels, W. Gartner, K. P. Hofmann, O. P. Ernst, J. Biol. Chem. 2000, 275, 19 713.
21. B. Borhan, M. L. Souto, H. Imai, Y. Shichida, K. Nakanishi, Science 2000, 288, 2209.
22. M. L. Souto, J. Um, B. Borhan, K. Nakanishi, Helv. Chim. Acta 2000, 83, 2617.
23. H. Zhang, K. A. Lerro, T. Yamamoto, T. H. Lien, L. Sastry, M. A. Gawinowicz, K. Nakanishi, J. Am. Chem. Soc. 1994, 116, 10 165.
24. H. Kakitani, T. Kakitani, S. Yomosa, J. Phys. Soc. Jpn. 1977, 42, 996.
25. M. Han, S. O. Smith, Biochemistry 1995, 34, 1425.
26. M. Han, Biochemistry 1997, 36, 7280.
27. Q. Tan, J. Lou, B. Borhan, E. Karnaukhova, N. Berova, K. Nakanishi, Angew. Chem. 1997, 109, 2190;
28. Angew. Chem. Int. Ed. Engl. 1997, 36, 2089.
29. J. Lou, M. Hashimoto, N. Berova, K. Nakanishi, Org. Lett. 1999, 1, 51.
30. V. Buss, K. Kolster, F. Terstegen, R. Vahrenhorst, Angew. Chem. 1998, 110, 1997;
31. Angew. Chem. Int. Ed. 1998, 37, 1893.
32. M. Ishiguro, J. Am. Chem. Soc. 2000, 122, 444.
33. V. Buss, Chirality 2001, 13, 13.
34. D. C. Teller, T. Okada, C. A. Behnke, K. Palczewski, R. E. Stenkamp, Biochemistry 2001, 40, 776.
35. L. C. Mollevanger, A. P. Kentgens, J. A. Pardoen, J. M. Courtin, W. S. Veeman, J. Lugtenburg, W. J. de Grip, Eur. J. Biochem. 1987, 163, 9.
36. S. O. Smith, I. Palings, V. Copie, D. P. Raleigh, J. Courtin, J. A. Pardoen, J. Lugtenburg, R. A. Mathies, R. G. Griffin, Biochemistry 1987, 26, 1606.
37. G. Grobner, I. J. Burnett, C. Glaubitz, G. Choi, A. J. Mason, A. Watts, Nature 2000, 405, 810.
38. M. Ito, Y. Katsuta, Y. Imamoto, Y. Shichida, T. Yoshizawa, Photochem. Photobiol. 1992, 56, 915.
39. T. Hiyama, M. Shinoda, H. Nozaki, J. Am. Chem. Soc. 1979, 101, 1599.
40. J. Tsuji, Synthesis 1983, 369.
41. A. W. Gibson, G. R. Humphrey, D. J. Kennedy, S. H. B. Wright, Synthesis 1991, 414.
42. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467.
43. F. Sato, Y. Kobayashi, Org. Syn. 1990, 69, 106.
44. B. Borhan, M. L. Souto, J. M. Um, B. Zhou, K. Nakanishi, Chem. Eur. J. 1999, 5, 1172.
45. G. A. Molander, Chem. Rev. 1992, 92, 29.
46. W. Boland, N. Schroer, C. Sieler, M. Feigel, Helv. Chim. Acta 1987, 70, 1025-1040.
47. L. Packer in Methods in Enzymology, Vol. 81 (Eds.: S. P. Colowick, N. O. Kaplan), Academic Press, 1982, p. 48.
48. S. Hu, P. J. Franklin, J. Wang, B. E. R. Silva, F. Derguini, K. Nakanishi, Biochemistry 1994, 33, 408.
49. H. Kandori, S. Matsuda, Y. Shichida, M. Ito, K. Tsukida, V. Baloghnair, K. Nakanishi, Biochemistry 1989, 28, 6460.