Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)

Pseurotins A(1) (1) and A(2) (2) were isolated from a culture broth of the fungal strain Aspergillus fumigatus WFZ-25 as stereoisomers of pseurotin A (3) in 2011. We also isolated 1 and 2 together with 3 from A. fumigatus OUPS-T106B-5 separated from the marine fish Mugil cephalus. In this study, we...

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Autores principales: Yamada, Takeshi, Ohshima, Mina, Yuasa, Kaori, Kikuchi, Takashi, Tanaka, Reiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4849078/
https://www.ncbi.nlm.nih.gov/pubmed/27070628
http://dx.doi.org/10.3390/md14040074
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author Yamada, Takeshi
Ohshima, Mina
Yuasa, Kaori
Kikuchi, Takashi
Tanaka, Reiko
author_facet Yamada, Takeshi
Ohshima, Mina
Yuasa, Kaori
Kikuchi, Takashi
Tanaka, Reiko
author_sort Yamada, Takeshi
collection PubMed
description Pseurotins A(1) (1) and A(2) (2) were isolated from a culture broth of the fungal strain Aspergillus fumigatus WFZ-25 as stereoisomers of pseurotin A (3) in 2011. We also isolated 1 and 2 together with 3 from A. fumigatus OUPS-T106B-5 separated from the marine fish Mugil cephalus. In this study, we re-examined the stereochemistry of 1 and 2 using chemical transformation and the CD spectra, and found the relationship between the CD Cotton effect and the absolute configurations of 1 and 2, which led us to revise the stereostructure of pseurotin A(2).
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spelling pubmed-48490782016-05-03 Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2) Yamada, Takeshi Ohshima, Mina Yuasa, Kaori Kikuchi, Takashi Tanaka, Reiko Mar Drugs Article Pseurotins A(1) (1) and A(2) (2) were isolated from a culture broth of the fungal strain Aspergillus fumigatus WFZ-25 as stereoisomers of pseurotin A (3) in 2011. We also isolated 1 and 2 together with 3 from A. fumigatus OUPS-T106B-5 separated from the marine fish Mugil cephalus. In this study, we re-examined the stereochemistry of 1 and 2 using chemical transformation and the CD spectra, and found the relationship between the CD Cotton effect and the absolute configurations of 1 and 2, which led us to revise the stereostructure of pseurotin A(2). MDPI 2016-04-09 /pmc/articles/PMC4849078/ /pubmed/27070628 http://dx.doi.org/10.3390/md14040074 Text en © 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yamada, Takeshi
Ohshima, Mina
Yuasa, Kaori
Kikuchi, Takashi
Tanaka, Reiko
Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)
title Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)
title_full Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)
title_fullStr Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)
title_full_unstemmed Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)
title_short Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A(2)
title_sort assignment of the cd cotton effect to the chiral center in pseurotins, and the stereochemical revision of pseurotin a(2)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4849078/
https://www.ncbi.nlm.nih.gov/pubmed/27070628
http://dx.doi.org/10.3390/md14040074
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