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Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample
Since its partial configurational assignment in 1964, pandamine has not been isolated or obtained by total synthesis. For decades, different works representing the structure of pandamine for illustrative purposes have lent different configurations to this molecule, causing tenacious confusion about...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10147048/ https://www.ncbi.nlm.nih.gov/pubmed/37110129 http://dx.doi.org/10.3390/metabo13040470 |
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author | Retailleau, Pascal Numbi Wa Ilunga, Evodie Fontaine, Véronique Gallard, Jean-François Le Pogam, Pierre |
author_facet | Retailleau, Pascal Numbi Wa Ilunga, Evodie Fontaine, Véronique Gallard, Jean-François Le Pogam, Pierre |
author_sort | Retailleau, Pascal |
collection | PubMed |
description | Since its partial configurational assignment in 1964, pandamine has not been isolated or obtained by total synthesis. For decades, different works representing the structure of pandamine for illustrative purposes have lent different configurations to this molecule, causing tenacious confusion about the structure of this ansapeptide. A comprehensive spectroscopic analysis of the authentic pandamine sample led to the complete and unambiguous assignment of its configuration, 59 years after its isolation. In addition to ascertaining and completing the initial structural deductions by a state-of-the-art set of analytical techniques, the purpose of this study is also to clarify the literature in a context in which various erroneous structures have been attributed to pandamine for half a century. While fully in agreement with Goutarel’s conclusions, the specific example of pandamine should serve as a cautionary tale to any chemist interested in natural products, encouraging access to initial structural assignments rather than relying solely on subsequent, possibly erroneous, structure depictions of a natural product. |
format | Online Article Text |
id | pubmed-10147048 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-101470482023-04-29 Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample Retailleau, Pascal Numbi Wa Ilunga, Evodie Fontaine, Véronique Gallard, Jean-François Le Pogam, Pierre Metabolites Article Since its partial configurational assignment in 1964, pandamine has not been isolated or obtained by total synthesis. For decades, different works representing the structure of pandamine for illustrative purposes have lent different configurations to this molecule, causing tenacious confusion about the structure of this ansapeptide. A comprehensive spectroscopic analysis of the authentic pandamine sample led to the complete and unambiguous assignment of its configuration, 59 years after its isolation. In addition to ascertaining and completing the initial structural deductions by a state-of-the-art set of analytical techniques, the purpose of this study is also to clarify the literature in a context in which various erroneous structures have been attributed to pandamine for half a century. While fully in agreement with Goutarel’s conclusions, the specific example of pandamine should serve as a cautionary tale to any chemist interested in natural products, encouraging access to initial structural assignments rather than relying solely on subsequent, possibly erroneous, structure depictions of a natural product. MDPI 2023-03-24 /pmc/articles/PMC10147048/ /pubmed/37110129 http://dx.doi.org/10.3390/metabo13040470 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Retailleau, Pascal Numbi Wa Ilunga, Evodie Fontaine, Véronique Gallard, Jean-François Le Pogam, Pierre Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample |
title | Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample |
title_full | Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample |
title_fullStr | Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample |
title_full_unstemmed | Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample |
title_short | Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample |
title_sort | clarifying the configuration of pandamine by an extensive spectroscopic reinvestigation of the authentic 1964 sample |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10147048/ https://www.ncbi.nlm.nih.gov/pubmed/37110129 http://dx.doi.org/10.3390/metabo13040470 |
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