Model-Free Approach for the Configurational Analysis of Marine Natural Products

• Published in: Marine drugs Vol. 19; no. 6; p. 283
• Main Authors: Köck, Matthias, Reggelin, Michael, Immel, Stefan
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 21-05-2021; MDPI
• Subjects: Amines; Analysis; Approximation; configurational analysis; Configurations; Connectors; Couplings; Distance; distance bounds driven dynamics; distance geometry; Geometry; Mathematical models; Natural products; NMR; NMR spectroscopy; NOE data; Nuclear magnetic resonance; Parameters; Proteins; Simulation
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md19060283

The NMR-based configurational analysis of complex marine natural products is still not a routine task. Different NMR parameters are used for the assignment of the relative configuration: NOE/ROE, homo- and heteronuclear J couplings as well as anisotropic parameters. The combined distance geometry (DG) and distance bounds driven dynamics (DDD) method allows a model-free approach for the determination of the relative configuration that is invariant to the choice of an initial starting structure and does not rely on comparisons with (DFT) calculated structures. Here, we will discuss the configurational analysis of five complex marine natural products or synthetic derivatives thereof: the cis-palau’amine derivatives 1a and 1b, tetrabromostyloguanidine (1c), plakilactone H (2), and manzamine A (3). The certainty of configurational assignments is evaluated in view of the accuracy of the NOE/ROE data available. These case studies will show the prospective breadth of application of the DG/DDD method.