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

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

doi:10.1021/acs.orglett.0c00098

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 journal › Article › peer-review

11 Scopus citations

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 language	English (US)
Pages (from-to)	1516-1519
Number of pages	4
Journal	Organic Letters
Volume	22
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.0c00098
State	Published - Feb 21 2020
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D",

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.",

author = "Shingare, {Rahul D.} and Victor Aniebok and Lee, {Hsiau Wei} and MacMillan, {John B.}",

note = "Funding Information: We acknowledge NIH Grant R01CA225960 and R01CA1499833for supporting this work and NIH Grant S10OD018455 for supporting the acquisition of the Bruker 800 MHz NMR. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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AU - Shingare, Rahul D.

AU - Aniebok, Victor

AU - Lee, Hsiau Wei

AU - MacMillan, John B.

N1 - Funding Information: We acknowledge NIH Grant R01CA225960 and R01CA1499833for supporting this work and NIH Grant S10OD018455 for supporting the acquisition of the Bruker 800 MHz NMR. Publisher Copyright: Copyright © 2020 American Chemical Society.

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

Abstract

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