X-ray crystal structure of a hindered 7-cis isomer of vitamin A. 7-cis-8-fluororetinal

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4103-4104

  Simmons, Charles J ^a   Colmenares, Leticia U ^b   Liu, R S H ^b  

^a BRIGHAM YOUNG UNIVERSITY HAWAII   (United States)

^b UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 CIS 8 FLUORORETINAL; OPSIN; RETINAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CIS ISOMER; CRYSTAL STRUCTURE; DRUG CONFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

EID: 0029920050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00766-6     Document Type: Article

References (20)

1. Trehan, A.; Mirzadegan, T.; Liu, R. S. H. Tetrahedron 1990, 46, 3769-3780.
2. (a) Liu, R. S. H.; Matsumoto, H.; Kini, A.; Asato, A. E.; Denny, M.; Kropf, A.; deGrip, W. J. Tetrahedron 1984, 40, 473-482;
3. (b) Liu, R. S. H.; Mirzadegan, T. J. Am. Chem. Soc. 1988, 110, 8617-8623.
4. (a) Matsumoto, H.; Liu, R. S. H.; Simmons, C. J.; Seff., K. J. Am. Chem. Soc. 1980, 102, 4259-4262;
5. (b) Simmons, C. J.; Liu, R. S. H.; Denny, M.; Seff, K. Acta Crystalllogr. 1981, Sect. B37, 2197-2205;
6. (c) Simmons, C. J.; Asato, A. E.; Liu, R, S, H. Acta Crystallogr. 1986, C42, 711-715; 1558-1563. For 11-cis-retinal, see: Gilardi, R. D.; Karle, I. L.; Karle, J. Acta Crystallogr. 1972, B28, 2605-2612.
7. (c) Simmons, C. J.; Asato, A. E.; Liu, R, S, H. Acta Crystallogr. 1986, C42, 711-715; 1558-1563. For 11-cis-retinal, see: Gilardi, R. D.; Karle, I. L.; Karle, J. Acta Crystallogr. 1972, B28, 2605-2612.
8. (a) Maeda, A.; Ogurusu, T.; Shichida, Y.; Tokunaga, F.; Yoshizawa, T. FEBS Lett. 1978, 92, 77-80;
9. (b) Zhu. Y.; Liu, R. S. H. Biochemistry 1993, 32, 10233-10238.
10. Liu, R. S. H.; Asato, A. E. in "Chemistry and Biology of Synthetic Retinoids" eds. Dawson, M. & Okamura, W. H., CRC Press, 1990, 51-75.
11. (a) Colmenares, L. U.; Asato, A. E.; Denny, M.; Mead, D.; Zingoni, J. P.; Liu, R. S. H. Biochem. Biophys. Res. Comm. 1991, 179, 1337-1343;
12. (b) Colmenares, L. U.; Liu, R. S. H. Tetrahedron 1996, 52, 109-118.
13. -1, F(000) = 328. X-ray diffraction data were collected at 160 K, λ(Mo, Kα) - 0.71073 Å, θ-2θ scan mode to 2θmax = 45̊, crystal size = 0.48 × 0.48 × 0.16 mm. Of 2261 unique reflections collected, 1141 had I > 3.5σ(I). The structure was solved using the direct methods programs in Texasan and refined by full-matrix least-square procedures. Final values of the observed data are R = 0.083 and Rw = 0.079; S = 4.93.
14. Selected bond lengthes: 1,2 = 1.52(1), 2,3 = 1.42(1), 3,4 = 1.50 (1), 4,5 = 1.49(1), 5.6 = 1.32(1), 6,1 = 1.56(1), 6,7 = 1.48(1), 7,8 = 1.31(1), 8,9 = 1.45 (1), 8,F19 = 1.391(9), 9,10 = 1.34(1), 10,11 = 1.45(1), 11,12 = 1.36(1), 12,13 = 1.48(1), 13,14 = 1.35(1), 14,15 = 1.44(1) Å; bond angles: 1,6,5 = 122.6(8), 1,6,7 = 114.6(9), 5,6,7 = 122.8(8), 6,7,8 = 125.8(9), 7,8,9 = 133.4(9), 7,8,F19 = 116.0(8), 9,8,F19 = 110.6(8), 8,9,10 = 121.2(9), 9,10,11 = 127.4(9), 10,11,12 = 122.4(9), 12,13,14 = 115.9(9), 13,14,15 = 115.9(9), 14,15,O22 = 125(1)°.
15. (a) Honig, B.; Hudson, B.; Sykes, B. D.; Karplus, M. Proc. Natl. Acad. Sci., USA 1971, 68, 1289-1293;
16. (b) Rowen III, R.; Sykes, B. D.; Warshel, A.; Karplus, M. Biochemistry 1974, 13, 970-981.
17. Liu, R. S. H.; Zingoni, J. P.; Kini, A.; Trammell, M.; Chu, D.; Asato, A. E.; Bopp, T. T. J. Org. Chem. 1983, 48, 4817-4821.
18. (a) Heyman, R. A.; Mangelsdorf, D. J.; Dyck, J. A.; Stein, R. B.; Eichelle, G.; Evans, R.M.; Thaller, C. Cell 1992, 68, 397-406;
19. (b) Allenby, G.; Bocquel, M.-T.; Saunders, M.; Kazmer, S.; Speck, T.; Rosenberger, M.; Lovey, A.; Kastner, P.; Grippo, J. F.; Chambon, P.; Levein, A. A. Proc. Natl. Acad. Sci., USA 1993, 90, 30-34.
20. The work was partially supported by a grant from U. S. Public Health Services (DK-17806).