New hindered isomers of 3-dehydroretinal (Vitamin A2)

Tetrahedron

Volumn 52, Issue 23, 1996, Pages 7809-7816

  Chen, Rong Liang ^a   Liu, Robert S H ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDRORETINOL; RETINOL;

ARTICLE; CHROMATOPHORE; ISOMERISM; PHOTOCHEMISTRY; PHOTOSENSITIVITY; PRIORITY JOURNAL; VITAMIN METABOLISM;

EID: 0030032720     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00355-9     Document Type: Article

References (26)

1. Ramamurthy, V.; Butt, Y.; Yang, C.; Yang, P.; Liu, R. S. H. J. Org. Chem. 1979, 38, 1247-1249.
2. (a) Trehan, A.; Liu, R. S. H. Tetrahedron Lett. 1988, 29, 419-422;
3. (b) Trehan, A.; Mirzadegan, T.; Liu, R. S. H. Tetrahedron 1990, 46, 3769-3780.
4. Ramamurthy, V.; Liu, R. S. H. Tetrahedron Lett. 1973, 441-444.
5. (a) Schwieter, U.; von Planta, C.; Ruegg, R.; Isler, O. Helv. Chim. Acta 1962, 45, 528-541, 541-548;
6. (b) Mayer, H.; Isler, O. in "Carotenoids," Birkhauser Verlag Basel, 1971, p. 325.
7. Wald, G. Fed. Proc. 1953, 12, 606-611.
8. Liu, R. S. H.; Asato, A. E.; Denny, M. J. Am. Chem. Soc. 1977, 99, 4865-4867.
9. Chen, R.-L.; Liu, R. S. H. Tetrahedron Lett. 1994, 35, 6251-6254.
10. Broom, S. J.; Ede, R. M.; Wilkins, A. L. Tetrahedron Lett. 1989, 33, 3197-3201.
11. Greene, T. W. "Protective Groups in Organic Synthesis," Wiley, New York, 1981, p. 124.
12. Liu, R. S. H.; Asato, A. E. Methods Enzymol. 1982, 88, 506-516.
13. Gollnick, K. Adv. Photochem. 1968, 6, 1-122.
14. Jensen, N.; Wilbrandt, R.; Bensasson, R. V. J. Am. Chem. Soc. 1989, 111, 7877-7888.
15. Liu, R. S. H.; Asato, A. E. Tetrahedron 1984, 40, 1931-1969.
16. Ramamurthy, V.; Liu, R. S. H. J. Org. Chem. 1976, 41, 1862-1867.
17. Unpublished results of Denny, M.; Liu, R. S. H. cited in Mead, D.; Loh, R.; Asato, A. E.; Liu, R. S. H. Tetrahedron Lett. 1985, 26, 2873-2876.
18. Ramamurthy, V.; Liu, R. S. H. J. Am. Chem. Soc. 1976, 98, 2935-2942.
19. For configurational assignments along the entire polyene chain of retinoids based on chemical shift and coupling constant data, see ref. 13.
20. Achab, S.; Das, B. C. J. Chem. Soc., Chem. Comm. 1983, 391-392.
21. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
22. 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.
23. Nakayama, A.; Bopp, T. T.; Liu, R. S. H. J. Org. Chem. 1984, 49, 3424-3426.
24. (a) Azuma, M.; Azuma, K.; Kito, Y. Biochim. Biophys. Acta 1973, 295, 520-526;
25. (b) Matsumoto, H.; Asato, A. E.; Liu, R. S. H. Photochem. Photobiol. 1979, 29, 695-698.
26. Chen, R.-L.; Liu, R. S. H. submitted to Bioorg. Chem.; also Ph.D. thesis of Chen, R.-L., University of Hawaii, 1995. The absorption maxima of the new pigment analogs (porphyropsins) derived from the 7-cis isomers of DHR are: 7-cis (458 nm), 7,9-dicis (466 nm) and 7,11-dicis (475 nm).