Skip to main content

Tryptophan and Related Alkaloids

  • Chapter
Kynurenine and Serotonin Pathways

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 294))

Abstract

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).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Boyd, D.R., and Berchtold, G.A., 1979, Aromatization of arene 1,2-oxides. 1-Carboxy-and 1-carboalkoxybenzene oxides, J. Am. Chem. Soc., 101: 2470–2474, and references cited therein.

    Article  CAS  Google Scholar 

  • Chang, C.-J., Floss, H.G., Hurley, L.H., and Zmijewski, M., 1976, Application of long-range spin-spin couplings in biosynthetic studies, J. Org. Chem., 41: 2932–2934.

    Article  PubMed  CAS  Google Scholar 

  • Daly, J.W., Jerina, D.M., and Witkop, B., 1972, Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds, Experientia, 28: 1129–1264.

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • Hino, T., Kodato, S., Takahashi, T., Yamaguchi, H., and Nakagawa, M., 1978, Oxidative dimerization of Nb-methoxycarbonyltryptamines by dye-sensitized photooxygenation in formic acid. Synthesis of (±)-folicanthine and (±)-chimonanthine, Tetrah. Lett., 19: 4913–4916.

    Article  Google Scholar 

  • Hino, T., Taniguchi, M., Yamamoto, I., Yamaguchi, K., and Nakagawa, M., 1981, Cyclic tautomers of tryptamines and tryptophans. V. Formation and reactions of cyclic tautomers of cyclo-L-tryptophanyl-L-proline, Tetrah. Lett., 22: 2565–2568.

    Article  CAS  Google Scholar 

  • Jerina, D.M., and Daly, J.W., 1974, Arene oxides: a new aspect of drug metabolism, Science, 185: 573–582.

    Article  PubMed  CAS  Google Scholar 

  • Kodato, S., Nakagawa, M., Hongu, M., Kawate, T., and Hino, T., 1988, Total synthesis of (+)-fumitremorgin B, its epimeric isomers, and demethoxy derivatives, Tetrahedron, 44: 359–377.

    Article  CAS  Google Scholar 

  • Martin, L.L., Chang, C.-J., Floss, H.G., Mabe, J.A., Hagaman, E.W., and Wenkert, E., 1972, A 13C nuclear magnetic resonance study on the biosynthesis of pyrrolnitrin from tryptophan by pseudomonas, J. Am. Chem. Soc., 94: 8942–8944.

    Article  CAS  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.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Ito, M., Hasegawa, Y., Akashi, S., and Hino, T., 1984a, Total synthesis (+)-tryptoquivaline, Tetrah. Lett., 25: 3865–3868.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Kato, S., Fukazawa, H., Hasegawa, Y., Miyazawa, J., and Hino, T., 1985a, Oxidative transformation of tryptophan to 2-(2-aminopheny1)-2-pyrrolidone and kynurenine, Tetrah. Lett., 26: 5871–5874.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Kodato, S., Hongu, M., Kawate, T., and Hino, T., 1986b, Total synthesis of fumitremorgen B, Tetrah. Lett., 27: 6217–6220.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Liu, J.-J., and Hino, T., 1989, Total synthesis of (−)-eudistomin L and (−)-debromoeudistomin L, J. Am. Chem. Soc, 111: 2721–2722.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Liu, J.-J., Ogata, K., and Hino, T., 1986c, Synthetic approaches to eudistomins. Part 1. synthesis of l-amino-3-thiaindolo[2,3-a] quinolizidine, Tetrah. Lett., 27: 6087–6090.

    Article  CAS  Google 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 

  • Nakagawa, M., Maruyama, T., Hirakoso, K., and Hino, T., 1980, Reactivity of oxytryptamine conversion to 3-(o-aminopheny1)-2-pyrrolidone and kynurenamine, Tetrah. Lett., 21: 4839–4842.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Matsuki, K., and Hino, T., 1983a, A new synthesis of betacarboline, Tetrah. Lett., 34: 2171–2174.

    Article  Google Scholar 

  • Nakagawa, M., Sodeoka, M., Yamaguchi, K., and Hino, T., 1984b, Synthesis of the imidazo[l,2-α]indole-spirolactone ring system by oxidative double cyclization. A synthetic approach to tryptoquivalines, Chem. Pharmacol. Bull., 32: 1373–1384.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Sugumi, H., Kodato, S., and Hino, T., 1981, Oxidative dimerization of Nb-acyltryptophans; total synthesis and absolute configuration of ditryptophenaline, Tetrah. Lett., 22: 5323–5326.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Taniguchi, M., Sodeoka, M., Ito, M., Yamaguchi, K., and Hino, T., 1983b, Total synthesis of (+) — and (−)-tryptoquivaline G by biomimetic double cyclization, J. Am. Chem. Soc., 105: 3709–3710.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Yokoyama, Y., Kato, S., and Hino, T., 1984c, Oxidative transformation to 5-hydroxy-N-formylkynurenine, Heterocycles, 22: 59–62.

    Article  CAS  Google Scholar 

  • Nakagawa, M., Yokoyama, Y., Kato, S., and Hino, T., 1985b, Dye-sensitized photo-oxygenation of tryptophan, Tetrahedron, 41: 2125–2132.

    Article  CAS  Google Scholar 

  • Sakan, T., and Hayaishi, O., 1950, α-hydroxytryptophan, not an intermediate between tryptophan and kynurenine, J. Biol. Chem., 186: 177–180.

    PubMed  CAS  Google Scholar 

  • Taniguchi, M., Anjiki, T., Nakagawa, M., and Hino, T., 1984, Formation and reactions of the cyclic tautomers of tryptophans and tryptamines. VII. Hydroxylation of tryptophans and tryptamines, Chem. Pharm. Bull., 32: 2544–2554.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Plenum Press, New York

About this chapter

Cite this chapter

Nakagawa, M., Hino, T. (1991). Tryptophan and Related Alkaloids. In: Schwarcz, R., Young, S.N., Brown, R.R. (eds) Kynurenine and Serotonin Pathways. Advances in Experimental Medicine and Biology, vol 294. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5952-4_2

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-5952-4_2

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5954-8

  • Online ISBN: 978-1-4684-5952-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics