Köck, Matthias ; Reggelin, Michael ; Immel, Stefan (2021)
Model-free approach for the configurational analysis of marine natural products.
In: Marine Drugs, 19 (6)
doi: 10.3390/md19060283
Artikel, Bibliographie
Dies ist die neueste Version dieses Eintrags.
Kurzbeschreibung (Abstract)
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.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 2021 |
| Autor(en): | Köck, Matthias ; Reggelin, Michael ; Immel, Stefan |
| Art des Eintrags: | Bibliographie |
| Titel: | Model-free approach for the configurational analysis of marine natural products |
| Sprache: | Englisch |
| Publikationsjahr: | 2021 |
| Ort: | Basel |
| Verlag: | MDPI |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Marine Drugs |
| Jahrgang/Volume einer Zeitschrift: | 19 |
| (Heft-)Nummer: | 6 |
| Kollation: | 15 Seiten |
| DOI: | 10.3390/md19060283 |
| Zugehörige Links: | |
| Kurzbeschreibung (Abstract): | 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. |
| Freie Schlagworte: | configurational analysis, distance geometry, distance bounds driven dynamics, NMR spectroscopy, NOE data |
| Zusätzliche Informationen: | Dedicated to Prof. Dr. Horst Kessler on occasion of his 81st birthday. This article belongs to the Special Issue Configurational and Conformational Studies on the Structures of Marine Natural Products |
| Sachgruppe der Dewey Dezimalklassifikatin (DDC): | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Fachbereich(e)/-gebiet(e): | 07 Fachbereich Chemie 07 Fachbereich Chemie > Clemens-Schöpf-Institut > Fachgebiet Organische Chemie |
| Hinterlegungsdatum: | 15 Jan 2024 07:35 |
| Letzte Änderung: | 16 Jan 2024 07:54 |
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Verfügbare Versionen dieses Eintrags
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Model-Free Approach for the Configurational Analysis of Marine Natural Products. (deposited 12 Jan 2024 14:54)
- Model-free approach for the configurational analysis of marine natural products. (deposited 15 Jan 2024 07:35) [Gegenwärtig angezeigt]
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