Alkylated azulenic retinal and bacteriorhodopsin analogs

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 5-8

  Muthyala, Rajeev S ^b   Alam, Maqsudul ^a   Liu, Robert S H ^b  

^a UNIVERSITY OF HAWAII   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AZULENE; BACTERIORHODOPSIN; RETINAL;

ACYLATION; ALKYLATION; ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FLUORINATION; MOLECULAR RECOGNITION; NONHUMAN; REACTION ANALYSIS; VITAMIN METABOLISM;

EID: 0031983805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10561-5     Document Type: Article

References (18)

1. (a) Asato, A.E.; Li, X.Y.; Mead, D.; Patterson, G.M.L.; Liu, R.S.H. J. Am. Chem. Soc. 1990, 112, 7398;
2. (b) Liu, R.S.H.; Liu, C.W.; Li, X.Y.; Asato, A.E. Photochem. Photobiol. 1991, 54, 625.
3. (a) Hafner, K. Angew Chem. 1958, 170, 419;
4. (b) Rudolf, K.; Robinette, D.; Koenig, D. J. Org. Chem. 1987, 52, 641.
5. (a) Hunig, S.; Hafner, K.; Ort, B.; Muller, M. Liebigs. Ann. Chem. 1986, 1222;
6. (b) McDonald, R.N.; Petty, H. E.; Wolfe, N.L.; Paukstelis, J.V. J. Org. Chem. 1974, 39, 1877.
7. Amemiy, T.; Yasunami, M.; Takase, K. Chem. Lett. 1987, 587.
8. See, e.g., Liu, R.S.H.; Asato, A.E. Methods Enzymol. 1982, 88, 506.
9. Muthyala, R.; Liu, R.S.H. submitted to J. Fluorine Chem.
10. Asato A.E., Matsumoto H., Denny M., Liu R.S.H. J. Am. Chem. Soc. 100:1978;5957.
11. For a recent review, see: Nakanishi, K.; Crouch, R. Israel J. Chem. 1995, 35, 253.
12. It was reasoned that even under maximal conditions, such red-shifted pigment analogs might not have as large on OS value as bR: Liu, R.S.H.; Krogh, E.; Li, X.Y.; Mead, D.; Colmenares, L.U.; Thiel, J.R.; Ellis, J.; Wong, D.; Asato, A.E. Photochem. Photobiol. 1993, 58, 701.
13. Oesterhelt D., Braüchle C., Hampp N. Q. Rev. Biophys. 24:1991;425.
14. Colmenares L.U., Niemczura W., Asato A.E., Liu R.S.H. J. Phys. Chem. 100:1996;9175.
15. (a) Tierno, M.; Mead, D.; Asato, A.E.; Liu, R.S.H.; Sekiya, N.; Yoshihara, K.; Chang, C.W.; Nakanishi, K.; Govindjee, R.; Ebrey, T.G. Biochemistry 1990, 29, 5948;
16. (b) Francesch, A.; Lopez, S.; de Lera, A.R. J. Org. Chem. 1997, 62, 310.
17. 3, d, 3.0 Hz, 3H), 1.48 (C6-t-butyl, s, 9H) ppm.
18. The work was partially supported by grants from the Army Research Office (DAAHO4) and U. S. Public Health Services (DK-17806).