Probing the role of polyphenol oxidation in mediating insect-pathogen interactions. Galloyl-derived electrophilic traps for the Lymantria dispar nuclear polyhedrosis virus matrix protein polyhedrin

Ken S. Feldman, Aruna Sambandam, Katherine E. Bowers, Heidi M. Appel

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Abstract

Galloyl-derived orthoquinone probes have been designed, synthesized, and utilized in an ongoing study of insect-pathogen interactions. A stable galloyl-derived orthoquinone O-methyl ether modified with both acidic and fluorescent appendages was successful in trapping the model nucleophile cysteine, a test protein bearing a single cysteine residue, and the viral occlusion body matrix protein polyhedrin from Lymantria dispar nuclear polyhedrosis virus (LdNPV), a pathogen of the gypsy moth caterpillar (GMc). This latter observation may be related to the molecular mechanism by which gallotannins decrease LdNPV infectivity in GMc's. Sufficient site isolation was not achieved with a polymer-bound reactive galloyl hydroxyorthoquinone electrophile to permit similar nucleophile trapping to compete with oligomerization.

Original languageEnglish (US)
Pages (from-to)5794-5803
Number of pages10
JournalJournal of Organic Chemistry
Volume64
Issue number16
DOIs
Publication statusPublished - Aug 6 1999

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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