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

Jae Yoon Leem, Chiaki Nishimura, Shoichiro Kurata, Ichio Shimada, Ayako Kobayashi, Shunji Natori

Research output: Contribution to journalArticlepeer-review

68 Citations (Scopus)

Abstract

We purified a novel antibacterial substance from immunized adult Sarcophaga and determined its molecular structure to be N-β-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD). We synthesized 5-S-GAD enzymatically from N-β-alanyl-3,4-dihydroxyphenylalanine (β-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.

Original languageEnglish
Pages (from-to)13573-13577
Number of pages5
JournalJournal of Biological Chemistry
Volume271
Issue number23
DOIs
Publication statusPublished - 1996
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Cell Biology

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