Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample

• Published in: Metabolites Vol. 13; no. 4; p. 470
• Main Authors: Retailleau, Pascal, Numbi Wa Ilunga, Evodie, Fontaine, Véronique, Gallard, Jean-François, Le Pogam, Pierre
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 24.03.2023; MDPI
• Subjects: Alcohol; Alkaloids; Amino acids; ansapeptide; Chemical properties; Chemical Sciences; Cristallography; Euphorbiaceae; Health aspects; Medicinal Chemistry; Natural products; Nitrogen; Nuclear magnetic resonance spectroscopy; pandaceae; pandamine; peptide alkaloid; Solvents; Structure; structure reassessment; France; peptide alkaloid; pandaceae; pandamine; ansapeptide; structure reassessment
• ISSN: 2218-1989; 2218-1989
• DOI: 10.3390/metabo13040470

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.