Tryptophan and Related Alkaloids
Tryptophan is metabolized to a number of biologically important substances (Hayaishi, 1962, 1974). It is now well established that tryptophan is metabolized to NAD via formylkynurenine which was formed by the oxidative cleavage of the 2,3-bond of the indole ring catalyzed by tryptophan-2,3-dioxygenase. On the other hand, the hydroxylation of tryptophan at 5-position accompanied by the NIH shift is another important reaction catalyzed by tryptophan 5-hydroxylase (Daly et al., 1972; Jerina and Daly, 1974; Boyd and Berchtold, 1979). Furthermore, tryptophan also serves as an important precursor for the biosynthesis of indole alkaloids (Scheme 1).
KeywordsMethylene Blue Total Synthesis Acridine Orange Indole Alkaloid Quinone Imine
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- Gorman, M., and Lively, D.H., 1967, Pyrrolnitrin: a new mode of tryptophan metabolism, in: “Antibiotics” Vol. II, D. Gottlieb, and P.D. Shaw, eds., Springer-Verlag, New York, pp. 433–438.Google Scholar
- Hayaishi, O., ed., 1962, “Oxygenases” Academic Press, New York.Google Scholar
- Hayaishi, O., ed., 1974, “Molecular Mechanisms of Oxygen Activation”, Chapter 1, History and Scope, Academic Press, New York, pp. 1–29.Google Scholar
- Nakagawa, M., 1980, Oxygenation of tryptophan to formylkynurenine-dye-sensitized photooxygenation, in: “Biochemical and Medical Aspects of Tryptophan Metabolism”, Hayaishi, O., Ishimura, U., and Kido, R., eds., Elsevier/ North Holland, pp. 49–58.Google Scholar
- Nakagawa, M., Fukushima, H., Kawate, T., Hongu, M., Kodato, S., Une, T., Taniguchi, M., and Hino, T., 1986a, Synthetic approach to the total synthesis of fumitremorgins II synthesis of optically active pentacyclic intermediates and their dehydrogenation, Tetrah. Lett., 27: 3235–3238.CrossRefGoogle Scholar
- Nakagawa, M., Liu, J.-J., Ogata, K., and Hino, T., 1988, New evidence for the presence of a spiroindolenine intermediate in Pictet-Spengler reaction of Nb-hydroxytryptamine, J.C.S. Chem. Comm., 463–464.Google Scholar