Köck, Matthias ; Reggelin, Michael ; Immel, Stefan (2024)
The Advanced Floating Chirality Distance Geometry Approach ― How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products.
In: Marine Drugs, 2020, 18 (6)
doi: 10.26083/tuprints-00016986
Artikel, Zweitveröffentlichung, Verlagsversion
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Kurzbeschreibung (Abstract)
The configurational analysis of complex natural products by NMR spectroscopy is still a challenging task. The assignment of the relative configuration is usually carried out by analysis of interproton distances from NOESY or ROESY spectra (qualitative or quantitative) and scalar (J) couplings. About 15 years ago, residual dipolar couplings (RDCs) were introduced as a tool for the configurational determination of small organic molecules. In contrast to NOEs/ROEs which are local parameters (distances up to 400 pm can be detected for small organic molecules), RDCs are global parameters which allow to obtain structural information also from long-range relationships. RDCs have the disadvantage that the sample needs a setup in an alignment medium in order to obtain the required anisotropic environment. Here, we will discuss the configurational analysis of five complex natural products: axinellamine A (1), tetrabromostyloguanidine (2), 3,7-epi-massadine chloride (3), tubocurarine (4), and vincristine (5). Compounds 1–3 are marine natural products whereas 4 and 5 are from terrestrial sources. The chosen examples will carefully work out the limitations of NOEs/ROEs in the configurational analysis of natural products and will also provide an outlook on the information obtained from RDCs.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 2024 |
| Autor(en): | Köck, Matthias ; Reggelin, Michael ; Immel, Stefan |
| Art des Eintrags: | Zweitveröffentlichung |
| Titel: | The Advanced Floating Chirality Distance Geometry Approach ― How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products |
| Sprache: | Englisch |
| Publikationsjahr: | 15 Januar 2024 |
| Ort: | Darmstadt |
| Publikationsdatum der Erstveröffentlichung: | 2020 |
| Ort der Erstveröffentlichung: | Basel |
| Verlag: | MDPI |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Marine Drugs |
| Jahrgang/Volume einer Zeitschrift: | 18 |
| (Heft-)Nummer: | 6 |
| Kollation: | 22 Seiten |
| DOI: | 10.26083/tuprints-00016986 |
| URL / URN: | https://tuprints.ulb.tu-darmstadt.de/16986 |
| Zugehörige Links: | |
| Herkunft: | Zweitveröffentlichung DeepGreen |
| Kurzbeschreibung (Abstract): | The configurational analysis of complex natural products by NMR spectroscopy is still a challenging task. The assignment of the relative configuration is usually carried out by analysis of interproton distances from NOESY or ROESY spectra (qualitative or quantitative) and scalar (J) couplings. About 15 years ago, residual dipolar couplings (RDCs) were introduced as a tool for the configurational determination of small organic molecules. In contrast to NOEs/ROEs which are local parameters (distances up to 400 pm can be detected for small organic molecules), RDCs are global parameters which allow to obtain structural information also from long-range relationships. RDCs have the disadvantage that the sample needs a setup in an alignment medium in order to obtain the required anisotropic environment. Here, we will discuss the configurational analysis of five complex natural products: axinellamine A (1), tetrabromostyloguanidine (2), 3,7-epi-massadine chloride (3), tubocurarine (4), and vincristine (5). Compounds 1–3 are marine natural products whereas 4 and 5 are from terrestrial sources. The chosen examples will carefully work out the limitations of NOEs/ROEs in the configurational analysis of natural products and will also provide an outlook on the information obtained from RDCs. |
| Freie Schlagworte: | chirality, configurational analysis, distance geometry, NMR spectroscopy, NOE data, residual dipolar couplings |
| Status: | Verlagsversion |
| URN: | urn:nbn:de:tuda-tuprints-169864 |
| Zusätzliche Informationen: | This article belongs to the Special Issue Selected Papers from XVI MaNaPro and XI ECMNP |
| 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 14:07 |
| Letzte Änderung: | 16 Jan 2024 07:45 |
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- The Advanced Floating Chirality Distance Geometry Approach ― How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products. (deposited 15 Jan 2024 14:07) [Gegenwärtig angezeigt]
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