Synthesis and Investigation of the Abiotic Formation of Pyonitrins A–D | Zendy

Rahul D. Shingare | Zendy; Victor Aniebok | Zendy; HsiauWei Lee | Zendy; John B. MacMillan | Zendy

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

Author(s) -

Rahul D. Shingare,

Victor Aniebok,

HsiauWei Lee,

John B. MacMillan

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00098

Subject(s) - chemistry , pseudomonas , biosynthesis , stereochemistry , antifungal , biochemistry , bacteria , microbiology and biotechnology , enzyme , biology , genetics

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 15 N NMR spectroscopy.

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