Abstract
Vitamin A is vital for promotion of general growth, differentiation of epithelial tissues, visual function and reproduction. A connection between vitamin A and cancer was made 70 years ago when it was found that carcinomas of the stomach appeared in albino rats fed a vitamin A deficient diet (Fujimaki, 1926). The history of the carotenoids predates that of vitamin A. However, it was during the subsequent four years that the high vitamin A activity of carotene was demonstrated and its metabolism to vitamin A in the liver documented (for a review see Pawson, 1981). In 1930, Karrer presented a structural assignment for β-carotene and a year later, he proposed a structural formula for vitamin A alcohol (Karrer, 1938; Pawson, 1981).
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References
Bliss, A. F., 1951, The equilibrium between vitamin A alcohol and aldehyde in the presence of alcohol dehydrogenase, Arch. Biochem. Biophys., 31, 197.
Brändén, C.-L., Jörnvall, H., Eklund, H. and Furugren, B., 1975, Alcohol dehydrogenases in: “The Enzymes”, (Boyer, P. D. ed.) vol. 11, Academic Press, New York, pp 103–190.
Bridges, C. D. B., 1984, Retinoids in photosensitive systems, in: “The Retinoids”, (Sporn, M. B., Roberts, A. B. and Goodman, D. S. eds.) vol. 2, Academic Press, New York, pp 90–124.
Dawson, M. I. and Hobbs, P. D., 1990, Synthetic retinoic acid analogs: handling and characterization, in: “Methods in Enzymology”, (Packer, L. ed.) vol. 189 Academic Press, San Diego, pp 13–43.
Eklund, H. and Brändén, C.-L., 1983, The role of zinc in alcohol dehydrogenases in: “Zinc Enzymes”, (Spiro, T. G. ed.), John Wiley and Sons, New York, pp 123–152.
Eklund, H. and Brändén, C.-L., 1987, Alcohol dehydrogenase, in: “Biological Macromolecules and Assemblies”, (Jurnak, F. and McPherson, A. eds.), vol. 3, John Wiley and Sons, New York, pp 73–142.
Eklund, H., Plapp, B. V., Samama, J.-P. and Brändén, C.-L., 1982, Binding of substrate in a ternary complex of horse liver alcohol dehydrogenase, J. Biol. Chem., 257, 14349.
Eklund, H., Samama, J.-P. and Jones, T.A., 1984, Crystallographic investigations of nicotinamide adenine dinu-cleotide binding to horse liver alcohol dehydrogenase, Biochemistry, 23, 5982–5996.
Emerick, R. J., Zile, M., DeLuca, H. F., 1967, Formation of retinoic acid from retinol in the rat, Biochem. J. 102, 606–611.
Frolik, C. A., 1984, Metabolism of retinoids, in: “The Retinoids”, (Sporn, M. B., Roberts, A. B. and Goodman, D. S. eds.) vol. 2, Academic Press, New York, pp 177–208.
Fujimaki, Y., 1926, Formation of carcinoma in albino rats fed on deficient diets, J. Cancer Res., 10, 469–447.
Futterman, S., 1962, Enzymatic oxidation of vitamin A aldehyde to vitamin A acid, J. Biol. Chem. 237, 667–680.
Haldane, J. B. S., 1930, “Enzymes”, Longmans Green, London.
Hinson, J. A. and Neal, R. A., 1972, An examination of the oxidation of aldehydes by horse liver alcohol dehydrogenase, J. Biol. Chem., 247, 7106.
Jörnvall, H., 1970, Horse liver alcohol dehydrogenase, Eur. J. Biochem., 16, 25.
Karrer, P., 1938, “Organic Chemistry”, Elsevier, New York, pp 656–657 and 672–673.
Klinman, J. P., 1981, Probes and mechanism and transition state structure in the alcohol dehydrogenase reaction, CRC Crit. Rev. Biochem., 10, 39.
Light, D. R., Dennis, M. S., Forsythe, I. J., Liu, C. C., Green, D. W., Kratzer, D. A. and Plapp, B. V., 1992, α-Isoenzyme of alcohol dehydrogenase from monkey liver: cloning, expression, mechanism, coenzyme, and substrate specificity, J. Biol. Chem., 267, 12592.
Mezey, E. and Holt, P. R., 1971, The inhibitory effect of ethanol on retinol oxidation by human liver and cattle retina, Experimental and Molecular Pathology, 15, 148.
Moon, R. C. and Itri, L. M., 1984, Retinoids and cancer, in: “The Retinoids”, (Sporn, M. B., Roberts, A. B. and Goodman, D. S. eds.) vol. 2, Academic Press, New York, pp 327–372.
Oppenheimer, N. J. and Nenehan, G. T. M., 1995, Horse liver alcohol dehydrogenase-catalyzed aldehyde oxidation, in: “Enzymology and Molecular Biology of Carbonyl Metabolism 5”, (Weiner, H., Holmes, R. S. and Wermuth, G. eds.) Plenum Press, New York, pp 407–415.
Packer, L. ed., 1990a, “Methods in Enzymology” vol. 189 Academic Press, San Diego.
Packer, L. ed., 1990b, “Methods in Enzymology” vol. 190 Academic Press, San Diego.
Pawson, B. A., 1981, A historical introduction to the chemistry of vitamin A and its analogs (retinoids), Ann. New York Acad. Sci., 359, 1–8.
Pettersson, G., 1987, Liver alcohol dehydrogenase, CRC Crit. Rev. Biochem., 21, 349.
Pietruszko, R., 1979, Nonethanol substrates of alcohol dehydrogenase, in: “Biochemistry and Pharmacology of Ethanol”, vol. 1 (Majchrowicz, E. and Noble, E. P., eds.) Plenum Press, New York, pp 87–106.
Pocker, Y., 1989, Alcohol dehydrogenase: structure catalysis and site directed mutagenesis, in: “Metal Ions in Biological Systems”, (Sigel, H., ed.) Marcel Dekker, New York, pp 335–358.
Pocker, Y. and Bjorkquist, D. W., 1977a, Stopped-flow studies of carbon dioxide hydration and bicarbonate dehydration in H2O and D2O. Acid-base and metal ion catalysis, J. Am. Chem. Soc. 99, 6537.
Pocker, Y. and Bjorkquist, D. W., 1977b, Comparative studies of bovine carbonic anhydrase in H2O and D2O. Stopped-flow studies of the kinetics of interconversion of carbon dioxide and bicarbonate, Biochemistry 16, 5698.
Pocker, Y. and Fong, C. T. O., 1980, Kinetics of inactivation of erythrocyte carbonic anhydrase by sodium 2,6-pyridinedicarboxylate, Biochemistry 19, 2045.
Pocker, Y. and Janji, N., 1988, Differential modification of specificity in carbonic anhydrase, J. Biol. Chem. 263, 6169.
Pocker, Y. and Li, H., 1991, Kinetics and mechanism of methanol and formaldehyde interconversion and formaldehyde oxidation catalyzed by liver alcohol dehydrogenase, in: “Enzymology and Molecular Biology of Carbonyl Metabolism 3”, (Weiner, H., Wermuth, B. and Crabb, D. W. eds.) Plenum Press, New York, pp 315–325.
Pocker, Y. and Li, H., 1993, The catalytic specificity of liver alcohol dehydrogenase: vitamin A alcohol and vitamin A aldehyde activities, in: “Enzymology and Molecular Biology of Carbonyl Metabolism 4”, (Weiner, H., Crabb, D. W. and Flynn, T. G. eds.) Plenum Press, New York, pp 411–418.
Pocker, Y., Li, H. and Page, J. D., 1987, Liver alcohol dehydrogenase: metabolic and energetic aspects, in: “Advances in Biomedical Alcohol Research”, (Lindros, K. O., Ylikahri, R. and Kiianmaa, K. eds.) Pergamon Press, London, pp 181–185.
Pocker, Y. and Page, J. D., 1990, Zinc-activated alcohols in ternary complexes of liver alcohol dehydrogenase, J. Biol. Chem., 265, 22101–22108.
Pocker, Y. and Page, J. D., 1993, Fluorescence studies of ternary complexes of liver alcohol dehydrogenase, in: “Enzymology and Molecular Biology of Carbonyl Metabolism 4” (Weiner, H., Crabb, D. W. and Flynn, T. G. eds.) Plenum Press, New York, pp 513–521.
Pocker, Y. and Raymond, K. W., 1980, Kinetics and mechanistic studies of vitamin A alcohol to vitamin A aldehyde by liver alcohol dehydrogenase. The inhibition by ethanol and pyrazole, in: “Alcohol and Aldehyde Metabolizing Systems-IV”, (Thurman, R. G. ed.) Plenum Press, New York, pp 137–150.
Pocker, Y. and Raymond, K. W., 1985, Liver alcohol dehydrogenase: substrate inhibition and competition between substrates, Alcohol 2, 3.
Pocker, Y. Raymond, K. W. and Thompson III, W. H., 1986, Liver alcohol dehydrogenase: kinetic and mechanistic studies, in: “Zinc Enzymes”, (Bertini, I., Luchinat, C., Maret, W. and Zeppezauer, M. eds.) Birkhäuser, Boston, pp 435–449.
Roberts, A. B. and Sporn, M. B., 1984, Cellular biology and biochemistry of the retinoids in: “The Retinoids”, (Sporn, M. B., Roberts, A. B. and Goodman, D. S. eds.) vol. 2, Academic Press, New York, pp 209–286.
Segel, I. H., 1975, “Enzyme Kinetics”, John Wiley and Sons, New York.
Sporn, M. B., Roberts, A. B. and Goodman, D. S. eds., 1984a, “The Retinoids”, vol. 1, Academic Press, New York.
Sporn, M. B., Roberts, A. B. and Goodman, D. S. eds., 1984b, “The Retinoids”, vol. 2, Academic Press, New York.
Sund, H. and Thoerell, H., 1963, Alcohol dehydrogenases, in: “The Enzymes”, (Boyer, P. D., Lardy, H. and Myrback, K. eds.) vol. 7, Academic Press, New York, pp 25–83.
Theorell, H. and Yonetani, T., 1963, Liver alcohol dehydrogenase-DPN-pyrazole complex: a model of a ternary intermediate in the enzyme reaction, Biochemische Zeitschrife, 338, 537.
Wald, G., 1968, Molecular basis of visual excitation, Science, 162, 230–239.
Wratten, C. C. and Cleland, W. W., 1963, Product inhibition studies on yeast and liver alcohol dehydrogenases, Biochemistry, 2, 935.
Zeppezauer, M., 1986, The metal environment of alcohol dehydrogenase: aspects of chemical speciation and catalytic efficiency in a biological catalyst, in: “Zinc Enzymes”, (Bertini, I., Luchinat, C., Maret, W. and Zeppezauer, M. eds.) Birkhäuser, Boston, pp 417–434.
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Pocker, Y., Li, H. (1996). Mechanistic Enzymology of Liver Alcohol Dehydrogenase. In: Weiner, H., Lindahl, R., Crabb, D.W., Flynn, T.G. (eds) Enzymology and Molecular Biology of Carbonyl Metabolism 6. Advances in Experimental Medicine and Biology, vol 414. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-5871-2_38
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DOI: https://doi.org/10.1007/978-1-4615-5871-2_38
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