11,12-Difluororhodopsin and related odd-numbered fluororhodopsins. The use of J(F,F) for following a cis-trans isomerization process

Journal of the American Chemical Society

Volumn 121, Issue 24, 1999, Pages 5803-5804

  Colmenares, Leticia U ^a   Zou, Xiang Long ^a   Liu, Jin ^a   Asato, Alfred E ^a   Liu, Robert S H ^a   De Lera, Angel R ^b   Alvarez, Rosana ^b  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE; PROTEIN DERIVATIVE; RETINOL DERIVATIVE; RHODOPSIN; SCHIFF BASE;

ARTICLE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0033597635     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990495w     Document Type: Article

References (20)

1. Gerig, J. T. Prog. NMR Spectrosc. 1994, 293-370.
2. (a) Emsley, J. W.; Phillips, L.; Wray, V. Prog. Nucl. Magn. Reson. Spectrosc. 1977, 10, 85-756.
3. (b) Everett, T. S. In Chemistry of Organic Compounds II: A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; 1995, pp 1037-1086.
4. See, e.g., (a) Colmenares, L. U.; Liu, R. S. H. Tetrahedron 1996, 52, 109-118. (b) Colmenares, L. U.; Niemczura, W. P.; Asato, A. E.; Liu, R. S. H. J. Phys. Chem. 1996, 100, 9175-9180.
5. See, e.g., (a) Colmenares, L. U.; Liu, R. S. H. Tetrahedron 1996, 52, 109-118. (b) Colmenares, L. U.; Niemczura, W. P.; Asato, A. E.; Liu, R. S. H. J. Phys. Chem. 1996, 100, 9175-9180.
6. Asato, A. E.; Liu, R. S. H. Tetrahedron Lett. 1986, 27, 3337-3340.
7. Unpublished results of W. Middleton, communicated to RSHL, cited in ref 4.
8. See, e.g., Smart, B. Mol. Struct. Energ. 1986, 3, 141-191.
9. Francesch, A.; Alvarez, R.; Lopez, S.; de Lera, A. R. J. Org. Chem. 1997, 62, 310-319.
10. Julia, M.; Arnould, D. Bull. Soc. Chim. Fr. 1973, 746-750.
11. Groesbeek, M.; Rood, G. A.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1992, 111, 149-154.
12. (a) Sharma, G. M.; Roels, O. A. J. Org. Chem. 1973, 38, 3648-3651.
13. (b) Pattaroni, C.; Lauterwein, J. Helv. Chim Acta 1981, 64, 1969-1984.
14. 3
15. 2-13-demethylretinal (relative to the positive binding result of 13-demethylretinal).
16. 3b The small FOS for F-11 must, therefore, be due to the orientation of the 11-F substituent, directed away from the counterion toward a more open space of the binding pocket. This interpretation is consistent with the currently accepted model for rhodopsin, see, e.g., Shieh, T.; Han, M.; Sakmar, T. P.; Smith, S. O. J. Mol. Biol. 1997, 269, 373-384.
17. See, e.g., (a) Wald, G.; Brown, P. K. J. Gen. Physiol. 1953, 37, 189-200. (b) Rao, V. R.; Cohen, G. B.; Oprian, D. D. Nature 1994, 367, 639-642.
18. See, e.g., (a) Wald, G.; Brown, P. K. J. Gen. Physiol. 1953, 37, 189- 200. (b) Rao, V. R.; Cohen, G. B.; Oprian, D. D. Nature 1994, 367, 639-642.
19. F-12 signals for the random Schiff bases appear as an unresolved broad band slightly downfield from the retinal doublet.
20. See, e.g., Smith, S. O.; Courtin, J.; De Groot, H. J. M.; Gebhard, R.; Lugtenburg, J. Biochemistry 1991, 30, 7409-7415.