1. Academic Validation
  2. Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample

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

  • Metabolites. 2023 Mar 24;13(4):470. doi: 10.3390/metabo13040470.
Pascal Retailleau 1 Evodie Numbi Wa Ilunga 2 Véronique Fontaine 2 Jean-François Gallard 1 Pierre Le Pogam 3
Affiliations

Affiliations

  • 1 Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, France.
  • 2 Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles (ULB), Faculty of Pharmacy, Campus Plaine, Boulevard du Triomphe, 1050 Bruxelles, Belgium.
  • 3 Équipe "Chimie des Substances Naturelles" BioCIS, CNRS, Université Paris-Saclay, 17 Avenue des Sciences, 91400 Orsay, France.
Abstract

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.

Keywords

ansapeptide; pandaceae; pandamine; peptide alkaloid; structure reassessment.

Figures
Products
  • Cat. No.
    Product Name
    Description
    Target
    Research Area
  • HY-133905
    Natural Alkaloid