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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...

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Autores principales: Retailleau, Pascal, Numbi Wa Ilunga, Evodie, Fontaine, Véronique, Gallard, Jean-François, Le Pogam, Pierre
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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