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Recent Advances in the Synthesis of Retinoids and Visual Pigment Analogs Studies

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Carotenoids

Abstract

Recent activities in the field of synthetic retinoids have been stimulated by analog studies in the areas of cancer prevention using vitamin A and its derivatives,1 visual pigments2 and bacteriorhodopsin3 and other retinal containing proteins.4 It will not be possible to review here the variety of compounds available in the literature. Nor, will it be wise to repeat the effort of others who have already produced several extensive review articles.5 Instead, in this paper only efforts directed toward preparation of stereoisomers of vitamin A, a topic of interest here will be summarized.

Bioorganic Studies of Visual Pigments 10. For no. 9 in the series see ref. 2b. This work was supported by a grant from the U.S. Public Health Services (DK-17806).

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References

  1. M. B. Sporn and A. B. Roberts, Biological Methods for Analysis and Assay of Retinoids Relationships between Structure and Activity, in: “The Retinoids.” vol. 1, M. B. Sporn, A. B. Roberts, and D. S. Goodman, eds., Academic Press, Inc., N.Y., p. 236 (1984).

    Google Scholar 

  2. F. Derguini and K. Nakanishi. Synthetic Rhodopsin Analogs, Photobiochem. Photobiophys., 13:259 (1986).

    CAS  Google Scholar 

  3. R. S. H. Liu and A. E. Asato, The Binding Site of Opsin Based on Analog Studies with Isomeric, Fluorinated, Alkylated and Other Modified Retinals. in: “Chemistry and Biology of Synthetic Retinoids”, M. Dawson and W. H. Okamura, eds., CRC Press, in press.

    Google Scholar 

  4. R. K. Crouch, Studies of Rhodopsin and Bacteriorhodopsin Using Modified Retinals. Photochem. Photobiol., 44:803 (1986).

    Article  CAS  Google Scholar 

  5. Yu. A. Ovchinnikov, Bioorganic Chemistry of Rhodopsins, Pure Appl. Chem., 58: 725 (1986).

    Article  CAS  Google Scholar 

  6. See e.g., chapters in: “The Retinoids”, vol. 2, M. B. Sporn. A. B. Roberts, and D. S. Goodman, eds., Academic Press. Inc., N.Y. (1984).

    Google Scholar 

  7. F. Frickel, Chemistry and Physical Properties of Retinoids, in: “The Retinoids”, vol. 1, M. B. Sporn, A. B. Roberts, and D. S. Goodman, eds., Academic Press, Inc., N.Y., p. 8 (1984).

    Google Scholar 

  8. H. H. Kaegi, Synthesis of Retinoids Labelled with Radioisotopes, in: “The Retinoids”, vol. 1, M. B. Sporn, A. B. Roberts, and D. S. Goodman, eds., Academic Press, Inc., N.Y., p. 147 (1984).

    Google Scholar 

  9. R. Hubbard and G. Wald, Cis-trans Isomers of Vitamin A and Retinene in Vision, J. Gen. Physiol., 36:269 (1952–3).

    Article  CAS  Google Scholar 

  10. G. Wald, P. K. Brown, R. Hubbard, and W. Oroshnik, Hindered cis Isomers of Vitamin A and Retinene: the Structure of the Neo-b Isomer, Proc. Natl. Acad. Sci., USA, 41:438 (1955); 42:578 (1956).

    Article  CAS  Google Scholar 

  11. V. Ramamurthy and R. S. H. Liu, 7-Cis Isomers of Retinal via 7-cis- and 7,9-Dicis-b-C18-tetraene Ketones, Tetrahedron, 31:201 (1975).

    Article  CAS  Google Scholar 

  12. A. E. Asato and R. S. H. Liu, 7-cis,9-cis- and 7-cis, 9-cis, 13-cis-retinal. A Stereoselective Synthesis of 7-cis, 9-cis-b-Ionylideneacetaldehyde, J. Am. Chem. Soc., 97:4128 (1975).

    Article  CAS  Google Scholar 

  13. A. Kini, H. Matsumoto, and R. S. H. Liu, Doubly Hindered 7, 11-Dicis Isomers of Retinal. Synthesis, Properties and Interaction with Cattle Opsin, J. Am. Chem. Soc., 101:5078 (1975).

    Article  Google Scholar 

  14. A. Kini, H. Matsumoto, and R. S. H. Liu, 9, 11-Di-cis-retinal and 9, 11-Di-cis-rhodopsin, Bioorg. Chem., 9:406 (1980).

    Article  Google Scholar 

  15. A. E. Asato, A. Kini, M. Denny, and R. S. H. Liu, 7-cis, 9-cis, 11-cis-Retinal, all-cis-Vitamin A and 7-cis, 9-cis, 11-cis-12-Fluororetinal, J. Am. Chem. Soc., 105:2923 (1983).

    Article  CAS  Google Scholar 

  16. C. G. Knudsen, S. C. Carey, and W. H. Okamura, [1,5]-Sigmatropic Rearrangement of Vinylallenes: A Novel Route to Geometric Isomers of the Retinoids Possessing 11-cis Linkages Including 9-cis, 11-cis, 13-cis-Retinal, J. Am. Chem. Soc., 102:6355 (1980).

    Article  CAS  Google Scholar 

  17. P. K. Brown and G. Wald, The Neo-b Isomer of Vitamin A and Retinene. J. Biol. Chem., 222:865 (1956).

    CAS  Google Scholar 

  18. C. A. Frolik and J. A. Olson, Extraction, Separation and Chemical Analysis of Retinoids, in: “The Retinoids”, vol. 1, M. B. Sporn, A. B. Roberts and D. S. Goodman, eds., Academic Press. Inc., N.Y., p. 181 (1984).

    Google Scholar 

  19. R. C. Bruening, F. Derguini, and K. Nakanishi, Rapid High-performance Liquid Chromatographic Analysis of Retinal Mixtures, J. Chromatog., 361:437 (1986).

    Article  CAS  Google Scholar 

  20. R. S. H. Liu and A. E. Asato, Photochemistry and Synthesis of Stereoisomers of Vitamin A, Tetrahedron, 40:1931 (1984).

    Article  CAS  Google Scholar 

  21. G. Cainelli, G. Cardillo, and M. Orena, Synthesis of Compounds Containing the Isoprene Unit: A Stereospecific Synthesis of b-Ionylideneacetic Acid and 3-Dehydro-b-Ionylideneacetic Acid, a Key Intermediate to Abscisic Acid, J. Chem. Soc. Perkin. 1:1597 (1979).

    Article  Google Scholar 

  22. R. W. Dugger and C. H. Heathcock, A General Synthesis of 5,6-Dihydro-a-Pyrones, J. Org. Chem., 45:1181 (1980).

    Article  CAS  Google Scholar 

  23. G. Cainelli, G. Cardillo, M. Contento, P. Grasselli, and A. U. Ronchi, Synthesis of Compounds Containing the Isoprene Unit: A Synthesis of Vitamin A, Gazz. Chim. Ital., 103:117 (1973).

    CAS  Google Scholar 

  24. W. Oroshnik, The Synthesis and Configuration of Neo-b Vitamin A and Neoretinene b. J. Am. Chem. Soc., 87:2651 (1956).

    Article  Google Scholar 

  25. V. Ramamurthy, Y. Butt, C. Yang, P. Yang, and R. S. H. Liu, Preparation of 7-cis-Ionyl and -Ionylidene Derivatives and Other Sterically Hindered Olefins by One-Way Sensitized Geometric Isomerization, J. Org. Chem., 38:1247 (1973).

    Article  CAS  Google Scholar 

  26. D. Miller, M. Trammell, A. Kini, and R. S. H. Liu, Sulfone Routes to Sterically Hindered 7-cis Isomers of Vitamin A, Tetrahedron Lett., 22:409 (1981).

    Article  CAS  Google Scholar 

  27. R. S. H. Liu, A. E. Asato, and M. Denny, Medium- and Substituent-Directed Stereoselective Photoisomerization of Polyenes in the Vitamin A Series. Application of the Dellinger-Kasha Model, J. Am. Chem. Soc., 105: 4829 (1983).

    Article  CAS  Google Scholar 

  28. W. C. Still and C. Gennari, Direct Synthesis of Z-Unsaturated Esters. A Useful Modification of the Horner-Emmons Olefination, Tetrahedron Lett., 24:4405 (1983).

    Article  CAS  Google Scholar 

  29. D. Mead, A. E. Asato, M. Denny, R. S. H. Liu, Y. Hanzawa, T. Taguchi, A. Yamada, N. Kobayashi, A. Hosoda, and Y. Kobayashi, 9-cis and 11-cis Isomers of 18, 18, 18-, 19, 19, 19- and 20.20.20-Trifluororetinal, Tetrahedron Lett., 28:259 (1987).

    Article  CAS  Google Scholar 

  30. R. S. H. Liu, H. Matsumoto, A. Kini, A. E. Asato, M. Denny, A. Kropf, and W. deGrip, Seven New Hindered Isomeric Rhodopsins. A Reexamination of the Stereospecificity of the Binding Site of the Bovine Opsin, Tetrahedron, 40:473 (1984).

    Article  CAS  Google Scholar 

  31. H. Matsumoto and T. Yoshizawa, Recognition of Opsin to the Longitudinal Length of Retinal Isomers in the Formation of Rhodopsin, Vision Res., 18:607 (1978).

    Article  CAS  Google Scholar 

  32. H. Matsumoto, R. S. H. Liu, C. Simmons, and K. Seff, Longitudinal Restrictions of the Binding Site of Opsin as Measured with Retinal Isomers and Analogues, J. Am. Chem. Soc., 102:4259 (1980).

    Article  CAS  Google Scholar 

  33. See, E. A. Dratz and P. A. Hargrave, The Structure of Rhodopsin and the Rod Outer Segment Disk Membrane, Trends Biochem Sci., 8:128 (1983).

    Article  CAS  Google Scholar 

  34. P. A. Hargrave, J. H. McDowell, R. J. Feldmann, P. H. Atkinson, J. K. Mohana Rao, and P. Argos, Rhodopsin Protein and Carbohydrate Structure: Selected Aspects. Vision Res., 24:1487 (1984).

    Article  CAS  Google Scholar 

  35. R. S. H. Liu, A. E. Asato, M. Denny, and D. Mead, The Nature of Restrictions in the Binding Site of Rhodopsin, J. Am. Chem. Soc., 106:8298 (1984).

    Article  CAS  Google Scholar 

  36. The p-version of MMP2 of N. L. Allinger and Y. H. Yuh, Q.C.P.E., 11:395 (1983). The new program MMP2-(85) is available from Quantum Chemistry Program Exchange, Department of Chemistry. University of Indiana, Bloomington, IN 47405.

    Google Scholar 

  37. R. R. Rando and A. Chang, Studies on the Catalyzed Interconversions of Vitamin A Derivatives, J. Am. Chem. Soc., 105:2879 (1983).

    Article  CAS  Google Scholar 

  38. H. Matsumoto and T. Yoshizawa, Existence of a β-Ionone Ring-Binding Site in the Rhodopsin Molecule, Nature, 258:523 (1975).

    Article  CAS  Google Scholar 

  39. A. E. Asato, M. Denny, H. Matsumoto, T. Mirzadegan, W. C. Ripka, F. Crescitelli, and R. S. H. Liu, Study of the Shape of the Binding Site of Bovine Opsin Using 10-Substituted Retinal Isomers, Biochemistry, 25: 7021 (1986).

    Article  CAS  Google Scholar 

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© 1989 Plenum Press, New York

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Liu, R.S.H., Mirzadegan, T., Trehan, A. (1989). Recent Advances in the Synthesis of Retinoids and Visual Pigment Analogs Studies. In: Krinsky, N.I., Mathews-Roth, M.M., Taylor, R.F. (eds) Carotenoids. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0849-2_8

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  • DOI: https://doi.org/10.1007/978-1-4613-0849-2_8

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-8113-9

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