Skip to main content
NCBI home page
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1972 Jun;69(6):1569–1573. doi: 10.1073/pnas.69.6.1569

Structures of the Visual Chromophores and Related Pigments: A Conformational Basis of Visual Excitation

M Sundaralingam 1, C Beddell 1
PMCID: PMC426750  PMID: 4504370

Abstract

A detailed conformational analysis of the known crystal structures of vitamin A, carotenoid, and xanthenoid derivatives has been made. These studies suggest that the visual chromophore 11-cis retinal and its isomers may each occur in several different conformational states, which would be expected to have different lightabsorbing characteristics. The presence of such states for 11-cis retinal and all-trans retinal may contribute to the observed rhodopsin intermediates that have been characterized by different λmax values, and to the breadth of spectral response in scotopic and color vision.

Keywords: 11-cis retinal, vitamin A, xanthenoid, crystal structure, carotenoid

Full text

PDF
1569

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Abrahamson E. W., Ostroy S. E. The photochemical and macromolecular aspects of vision. Prog Biophys Mol Biol. 1967;17:179–215. doi: 10.1016/0079-6107(67)90007-7. [DOI] [PubMed] [Google Scholar]
  2. Anderson R. E. Is retinal-phosphatidyl ethanolamine the chromophore of rhodopsin? Nature. 1970 Aug 29;227(5261):954–955. doi: 10.1038/227954a0. [DOI] [PubMed] [Google Scholar]
  3. BLATZ P. E. THE ROLE OF CARBONIUM IONS IN COLOR RECEPTION. J Gen Physiol. 1965 May;48:753–760. doi: 10.1085/jgp.48.5.753. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. BROWN K. T., MURAKAMI M. A NEW RECEPTOR POTENTIAL OF THE MONKEY RETINA WITH NO DETECTABLE LATENCY. Nature. 1964 Feb 8;201:626–628. doi: 10.1038/201626a0. [DOI] [PubMed] [Google Scholar]
  5. Bart J. C., MacGillavry C. H. The crystal and molecular structure of canthaxanthin. Acta Crystallogr B. 1968 Dec 15;24(12):1587–1606. doi: 10.1107/s056774086800470x. [DOI] [PubMed] [Google Scholar]
  6. Bart J. C., MacGillavry C. H. The crystal structure of 15,15'-dehydrocanthaxanthin. Acta Crystallogr B. 1968 Dec 15;24(12):1569–1586. doi: 10.1107/s0567740868004693. [DOI] [PubMed] [Google Scholar]
  7. Blake C. C., Johnson L. N., Mair G. A., North A. C., Phillips D. C., Sarma V. R. Crystallographic studies of the activity of hen egg-white lysozyme. Proc R Soc Lond B Biol Sci. 1967 Apr 18;167(1009):378–388. doi: 10.1098/rspb.1967.0035. [DOI] [PubMed] [Google Scholar]
  8. Bownds D. Site of attachment of retinal in rhodopsin. Nature. 1967 Dec 23;216(5121):1178–1181. doi: 10.1038/2161178a0. [DOI] [PubMed] [Google Scholar]
  9. Dickerson R. E., Kopka M. L., Weinzierl J., Varnum J., Eisenberg D., Margoliash E. Location of the heme in horse heart ferricytochrome c by x-ray diffraction. J Biol Chem. 1967 Jun 25;242(12):3015–3018. [PubMed] [Google Scholar]
  10. Gilardi R., Karle I. L., Karle J., Sperling W. Crystal structure of the visual chromophores, 11-cis and all-trans retinal. Nature. 1971 Jul 16;232(5307):187–189. doi: 10.1038/232187c0. [DOI] [PubMed] [Google Scholar]
  11. Hall M. O., Bacharach A. D. Linkage of retinal to opsin and absence of phospholipids in purified frog visual pigment 500. Nature. 1970 Feb 14;225(5233):637–638. doi: 10.1038/225637a0. [DOI] [PubMed] [Google Scholar]
  12. Hirtenstein M. D., Akhtar M. Chromophore-environment interaction of visual pigments in model system. Nat New Biol. 1971 Sep 15;233(37):94–95. doi: 10.1038/newbio233094a0. [DOI] [PubMed] [Google Scholar]
  13. Honig B., Hudson B., Sykes B. D., Karplus M. Ring orientation in -ionone and retinals. Proc Natl Acad Sci U S A. 1971 Jun;68(6):1289–1293. doi: 10.1073/pnas.68.6.1289. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Honig B., Karplus M. Implications of torsional potential of retinal isomers for visual excitation. Nature. 1971 Feb 19;229(5286):558–560. doi: 10.1038/229558a0. [DOI] [PubMed] [Google Scholar]
  15. Hubbard R., Kropf A. THE ACTION OF LIGHT ON RHODOPSIN. Proc Natl Acad Sci U S A. 1958 Feb;44(2):130–139. doi: 10.1073/pnas.44.2.130. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. KRINSKY N. I. The lipoprotein nature of rhodopsin. AMA Arch Ophthalmol. 1958 Oct;60(4 Pt 2):688–694. doi: 10.1001/archopht.1958.00940080708014. [DOI] [PubMed] [Google Scholar]
  17. KROPF A., HUBBARD R. The mechanism of bleaching rhodopsin. Ann N Y Acad Sci. 1959 Nov 12;74(2):266–280. doi: 10.1111/j.1749-6632.1958.tb39550.x. [DOI] [PubMed] [Google Scholar]
  18. KROPF A., HUBBARD R. The mechanism of bleaching rhodopsin. Ann N Y Acad Sci. 1959 Nov 12;74(2):266–280. doi: 10.1111/j.1749-6632.1958.tb39550.x. [DOI] [PubMed] [Google Scholar]
  19. Lipscomb W. N., Reeke G. N., Jr, Hartsuck J. A., Quiocho F. A., Bethge P. H. The structure of carboxypeptidase A. 8. Atomic interpretation at 0.2 nm resolution, a new study of the complex of glycyl-L-tyrosine with CPA, and mechanistic deductions. Philos Trans R Soc Lond B Biol Sci. 1970 Feb 12;257(813):177–214. doi: 10.1098/rstb.1970.0020. [DOI] [PubMed] [Google Scholar]
  20. MATTHEWS R. G., HUBBARD R., BROWN P. K., WALD G. TAUTOMERIC FORMS OF METARHODOPSIN. J Gen Physiol. 1963 Nov;47:215–240. doi: 10.1085/jgp.47.2.215. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Poincelot R. P., Millar P. G., Kimbel R. L., Jr, Abrahamson E. W. Lipid to protein chromophore transfer in the photolysis of visual pigments. Nature. 1969 Jan 18;221(5177):256–257. doi: 10.1038/221256a0. [DOI] [PubMed] [Google Scholar]
  22. Steitz T. A., Henderson R., Blow D. M. Structure of crystalline alpha-chymotrypsin. 3. Crystallographic studies of substrates and inhibitors bound to the active site of alpha-chymotrypsin. J Mol Biol. 1969 Dec 14;46(2):337–348. doi: 10.1016/0022-2836(69)90426-4. [DOI] [PubMed] [Google Scholar]
  23. Vanderkooi G., Sundaralingam M. Biological membrane structure. II. A detailed model for the retinal rod outer segment membrane. Proc Natl Acad Sci U S A. 1970 Sep;67(1):233–238. doi: 10.1073/pnas.67.1.233. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Wald G. The molecular basis of visual excitation. Nature. 1968 Aug 24;219(5156):800–807. doi: 10.1038/219800a0. [DOI] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES