Purification and characterization of N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine, a novel antibacterial substance of Sarcophaga peregrina (flesh fly)

J Biol Chem. 1996 Jun 7;271(23):13573-7. doi: 10.1074/jbc.271.23.13573.

Abstract

We purified a novel antibacterial substance from immunized adult Sarcophaga and determined its molecular structure to be N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD). We synthesized 5-S-GAD enzymatically from N-beta-alanyl-3, 4-dihydroxyphenylalanine (beta-Ala-Dopa) and reduced glutathione (GSH). The antibacterial activity of 5-S-GAD was found to be due to its production of H2O2. This is a novel antibacterial mechanism as it differs from the mechanisms of known antibacterial peptides. Two possible roles of 5-S-GAD in insect immunity, suppression of bacterial growth and activation of a Rel family transcription factor, are proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Dihydroxyphenylalanine / analogs & derivatives*
  • Dihydroxyphenylalanine / chemistry
  • Dihydroxyphenylalanine / isolation & purification
  • Dihydroxyphenylalanine / pharmacology
  • Diptera / chemistry*
  • Diptera / immunology
  • Diptera / metabolism
  • Escherichia coli / drug effects
  • Escherichia coli / immunology
  • Glutathione / analogs & derivatives*
  • Glutathione / chemistry
  • Glutathione / isolation & purification
  • Glutathione / pharmacology
  • Hydrogen Peroxide / metabolism
  • Immunization
  • Molecular Structure

Substances

  • Anti-Bacterial Agents
  • N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine
  • Dihydroxyphenylalanine
  • Hydrogen Peroxide
  • Glutathione