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Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D
Rahul D Shingare1, Victor Aniebok1, Hsiau-Wei Lee1
1Department of Chemistry and Biochemistry , University of California, Santa Cruz , Santa Cruz , California 95064 , United States.
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.
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