Mechanisms of photoisomerization of polyenes in confined media: From organic glasses to protein binding cavities

Photochemistry and Photobiology

Volumn 83, Issue 1, 2007, Pages 2-10

  Liu, Robert S H ^a   Yang, Lan Ying ^a   Liu, Jin ^b,c  

^a UNIVERSITY OF HAWAII   (United States)

^b MURRAY STATE UNIVERSITY   (United States)

^c NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; BACTERIAL PROTEIN; BACTERIORHODOPSIN; DIPHENYLBUTADIENE; GLASS; PHOTOACTIVE YELLOW PROTEIN, BACTERIA; POLYENE; RHODOPSIN; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; VISUAL PROTEINS AND PIGMENTS; ZEOLITE;

CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CONFERENCE PAPER; ISOMERISM; PHOTOCHEMISTRY; PROTEIN BINDING; ULTRAVIOLET SPECTROPHOTOMETRY;

BACTERIAL PROTEINS; BACTERIORHODOPSINS; BUTADIENES; GLASS; ISOMERISM; MODELS, MOLECULAR; PHOTOCHEMISTRY; PHOTORECEPTORS, MICROBIAL; POLYENES; PROTEIN BINDING; RHODOPSIN; SPECTROPHOTOMETRY, ULTRAVIOLET; STILBENES; ZEOLITES;

EID: 34247863909     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2006-01-27-RA-786     Document Type: Conference Paper

References (43)

1. Mulliken, R. S. C. C. I. Roothaan (1947) The twisting frequency and the barrier height for free rotation in ethylene. Chem. Rev. 41, 219 231.
2. Busch, G. D., M. L. Applebury, A. A. Lamola P. Rentzepis (1972) Formation and decay of prelumirhodopsin at room temperature. Proc. Natl Acad. Sci. USA 69, 2802 2806.
3. Liu, R. S. H. A. E. Asato (1985) The primary process of vision and the structure of bathorhodopsin: A mechanism for photoisomerization. Proc. Natl Acad. Sci. USA 82, 259 263.
4. Warshel, A. (1976) Bicycle-pedal model for the first step in the vision process. Nature (London) 260, 679 683.
5. Müller, A. M., S. Lochbrunner, W. E. Schmid W. Fuss (1998) Low-temperature photochemistry of previtamin D: Hula-twist isomerization of a triene. Angew. Chem. Int. Ed. 37, 505 507.
6. Imamoto, Y., T. Kuroda, M. Kataoka, S. Shevyakov, G. Krishnamoorthy R. S. H. Liu (2003) Photoisomerization by hula-twist. 2,2′-dimethylstilbene and a related ring-fused analog. Angew. Chem. Int. Ed. 42, 3630 3633.
7. Krishnamoorthy, G., A. E. Asato R. S. H. Liu (2003) Conformational isomerizations of symmetrically substituted styrenes. No-reaction photoreactions by hula-twist. Chem. Commun., 2170 2171.
8. Krishnamoorthy, G., S. Schieffer, S. Shevyakov, A. E. Asato, K. Wong, J. Head R. S. H. Liu (2004) S-cis conformers in low temperature irradiation of dienes. Hula-twist mechanism of isomerization. Res. Chem. Interm. 30, 397 405.
9. Liu, R. S. H. G. S. Hammond (2005) Reflection on medium effects on photochemical reactivity. Acc. Chem. Res. 38, 396 403.
10. Yee, W. A., S. L. Hug D. S. Kliger (1988) Direct and sensitized photoisomerization of 1,4-diphenylbutadienes. J. Am. Chem. Soc. 110, 2164 2169.
11. Yang, L.-Y., R. S. H. Liu, K. J. Bowman, N. L. Wendt J. Liu (2005) New aspects of diphenylbutadiene photochemistry. Regioselective hula-twist photoisomerization. J. Am. Chem. Soc. 127, 2404 2405.
12. Mazzucato, U. F. Momicchioli (1991) Rotational isomerism in trans-1,2-diarylethylenes. Chem. Rev. 91, 1679 1719.
13. Waldeck, D. H. (1991) Photoisomerization dynamics of stilbenes. Chem. Rev. 91, 415 436.
14. Malkin, S. E. Fischer (1964) Temperature dependence of photoisomerization. III. Direct and sensitized photoisomerization of stilbenes. J. Phys. Chem. 68, 1153 1163.
15. Yang, L.-Y., M. Harigav, Y. Imamoto, M. Kataoka, T.-I. Ho, E. Andrioukhina, O. Federova, S. Shevyakov R. S. H. Liu (2006) 1,2-Diarylethylenes in hula-twist photoisomerization. Photochem. Photobiol. Sci. 5, 874 882.
16. Syamala, M. S., S. Devanathan V. Ramamurthy (1986) Modification of the photochemical behavior of organic molecules by cyclodextrin: Geometric isomerization of stilbenes and alkyl cinnamates. J. Photochem. 34, 219 229.
17. Seltzer, S. (1987) MNDO barrier height for catalyzed bicycle-pedal, hula-twist and ordinary cis-trans isomerizations of protonated retinal Schiff base. J. Am. Chem. Soc. 109, 1627 1631.
18. Odani, T., A. Matsumoto, K. Sada M. Miyata (2001) One way E,Z-isomerization of bis(n-butylammonium) (Z,Z)-muconate under photoirradiation in the crystalline state. Chem. Commun., 2004 2005.
19. Harada, J. K. Ogawa (2004) X-ray diffraction analysis of non-equilibrium states in crystals: Observation of an unstable conformer in flash-cooled crystals. J. Am. Chem. Soc. 126, 3539 3544.
20. Harada, J., K. Uekusa Y. Ohashi (1999) X-ray analysis of structural changes in photochromic salicylideneaniline crystals. J. Am. Chem. Soc. 121, 5809 5810.
21. Kaupp, G. J. Schmeyers (2000) The solid-state E/Z photoisomerization of 1,2-dibenzoylethene. J. Photochem. Photobiol. 59, 15 19.
22. Harada, J. (2005) A conference report presented at the PacifiChem Conference, Honolulu, December 18, 2005.
23. Borgstahl, G. E. O., D. R. Williams E. D. Getzoff (1995) 1.4 Å Structure of photoactive yellow protein, a cytosolic photoreceptor: Unusual fold, active site and chromophore. Biochemistry 34, 6278 6287.
24. Genick, U. K., S. M. Soltis, P. Kuhn, I. L. Canestrelli E. D. Getzoff (1998) Structure at 0.85 Å resolution of an early protein photocycle intermediate. Nature 392, 206 209.
25. Genick, U. K., G. E. O. Borgstahl, K. Ng, Z. Ren, C. Pradervand, P. M. Burke, V. Srajer, T. Y. Teng, W. Schildkamp, D. E. McRee, K. Moffat E. D. Getzoff (1997) Structure of a protein photocycle intermediate by millisecond time-resolved crystallography. Science 275, 1471 1475.
26. Anderson, S., V. Srajer K. Moffat (2004) Structural heterogeneity of cryotrapped intermediates in the bacterial blue light photoreceptor, photoactive yellow protein. Photochem. Photobiol. 80, 7 14.
27. Liu, R. S. H. (2001) Photoisomerization by hula-twist: A fundamental supramolecular photochemical reaction. Acc. Chem. Res. 34, 555 562.
28. Paling, I., J. A. Pardoen, E. van den Berg, C. Winkel, J. Lugtenburg R. A. Mathies (1987) Assignment of fingerprint vibrations in the resonance Raman spectra of rhodopsin, isorhodopsin and bathorhodopsin: Implications for chromophore structure and environment. Biochemistry 26, 2544 2556.
29. Shichida, Y., S. Matuoka T. Yoshizawa (1984) Formation of photorhodopsin, a precursor of bathorhodopsin. Photobiochem. Photobiophys. 7, 221 228.
30. Warshel, A. N. Barboy (1982) Energy storage and reaction pathways in the first step of the vision process. J. Am. Chem. Soc. 104, 1469 1476.
31. Yamada, A., T. Yamato, T. Kakitani S. Yamamoto (2004) Torsional potential works in rhodopsin. Photochem. Photobiol. 79, 476 486.
32. Palczewski, K., T. Kumasaha, 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 (2000) Crystal structure of rhodopsin: A G protein-coupled receptor. Science 289, 739 745.
33. Okada, T., Y. Fujiyoshi, M. Silow, J. Navarro, E. M. Landau Y. Shichida (2002) Functional role of internal water molecules in rhodopsin revealed by x-ray crystallography. Proc. Natl. Acad. Sci., USA 99, 5982 5987.
34. Teller, D. C., T. Okada, C. A. Behnke, K. Palczewski R. E. Stenkamp (2001) Advances in determination of a high-resolution three-dimensional structure of rhodopsin, a model of G-protein-coupled receptors (GPCRs). Biochemistry 40, 7761 7772.
35. Liu, R. S. H. L. U. Colmenares (2003) The molecular basis for the high photosensitivity of rhodopsin. Proc. Natl. Acad. Sci., USA 100, 14639 14644.
36. Mathies, R. A. J. Lugtenburg (2000) The primary photoreaction of rhodopsin. In Handbook of Biological Physics (Edited by D. G. Stavenga, W. J. deGrip E. N. Pugh, Jr. vol. 3, pp. 55 90. Elsevier Science, Amsterdam.
37. Kukura, P., D. W. McCamant, S. Yoon, D. B. Wandschneider R. A. Mathies (2005) Structural observation of the primary isomerization in vision with femtosecond-stimulated Raman. Science 310, 1006 1009.
38. Nakamichi, H. T. Okada (2006) Crystallographic analysis of primary visual photochemistry. Angew. Chem. Intern. Ed., 45, 4270 4273, and personal communication by Dr. Okada to RL.
39. Liu, R. S. H., G. S. Hammond L. U. Colmenares (2005) Possible role of the 11-cis-retinyl conformation in controlling the dual decay processes of excited rhodopsin. Proc. Natl. Acad. Sci., USA 102, 10783 10787.
40. Schulten, K. P. A. Tavan (1978) Mechanism for light-driven proton pumping of Halobacterium halobium. Nature (London) 272, 85 86.
41. Edman, K., P. Nollert, A. Royant, H. Belrahli, E. Peboy-Peyoula, J. Hadju, R. Neutze E. M. Landau (1999) High resolution X-ray structure of an early intermediate in the bacteriorhodopsin photocycle. Nature 401, 822 826.
42. Lueke, H., B. Schobert, H. T. Richter, J. P. Cartailler J. K. Lanyi (1999) Structure of bacteriorhodopsin at 1.55 Å resolution. J. Mol. Biol. 291, 899 911.
43. Liu, R. S. H. D. Browne (1986) A bioorganic view of the chemistry of vision: HT-n and BP-m,n mechanisms for reactions of confined, anchored polyenes. Acc. Chem. Res. 19, 42 48.