Papain Inhibition by New α-Methylene-γ-Lactone Carbohydrate Derivatives

  • Amélia P. Rauter
  • Maria S. Pais
  • Christina Duarte
  • Ana Ana Eusébio
  • Lígia Pinto
  • Christina Simões
  • Joaquim S. Cabral
Part of the NATO ASI Series book series (volume 18)

Abstract

Naturally occurring sesquiterpenes with α-methylene-γ-lactone units in its structure are known to exhibit a diversity of biological activities, namely cytostatic and anti-helmintic, and to act as plant growth regulators (Gross 1975; Hoffmann and Rube 1985). The mechanism of its action consists of an irreversible inhibition of sulfhydryl enzymes by a Michael-type reaction, in which the electrophilic methylene group is added to the sulfhydryl group of the enzyme.

Keywords

Carbohydrate Hydroxide Carbonyl Sodium Hydroxide Tetrahydrofuran 

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References

  1. Gross D (1975) Growth regulation substances of plant origin. Phytochem 14:2105–2112CrossRefGoogle Scholar
  2. Hoffmann HMR and Rube J (1985) Synthesis and biological activity of α-methylene-γ-butyrolactones. Angew Chem Int Ed Engl 24:99–110Google Scholar
  3. Rauter AP, Figueiredo JA, Ismael I, Pais MS, Gonzalez AG, Diaz J and Barrera JB (1987) Synthesis of α-methylene-γ-lactones in furanosidic systems. J Carbohydr Chem 6:259–272CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1988

Authors and Affiliations

  • Amélia P. Rauter
    • 1
  • Maria S. Pais
    • 1
  • Christina Duarte
    • 1
  • Ana Ana Eusébio
    • 1
  • Lígia Pinto
    • 1
  • Christina Simões
    • 1
  • Joaquim S. Cabral
    • 2
  1. 1.Departamento de Química da Faculdade de Ciências de Lisboa, Centro de Engenharia Biológica, INICUniversidade de LisboaLisboa CodexPortugal
  2. 2.Laboratório de Engenharia BioquímicaInstituto Superior Técnico da Universidade Técnica de LisboaLisboa CodexPortugal

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