Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D

Rahul D. Shingare, Victor Aniebok, Hsiau Wei Lee, John B. MacMillan

Research output: Contribution to journalArticle

Abstract

Pyonitrins A-D are recently isolated natural products from the insect-associated Pseudomonas protegens strain, which were isolated from complex fractions that exhibited antifungal activity via an in vivo murine candidiasis assay. Genomic studies of Pseudomonas protegens suggested that pyonitrins A-D are formed via a spontaneous nonenzymatic reaction between biosynthetic intermediates of two well-known natural products pyochelin and pyrrolnitrin. Herein we have accomplished the first biomimetic total synthesis of pyonitrins A-D in three steps and studied the nonenzymatic formation of the pyonitrins using 15N NMR spectroscopy.

Original languageEnglish (US)
Pages (from-to)1516-1519
Number of pages4
JournalOrganic Letters
Volume22
Issue number4
DOIs
StatePublished - Feb 21 2020
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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