The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products
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 (<i>J</i>...
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MDPI AG
2020-06-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/6/330 |
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| author | Matthias Köck Michael Reggelin Stefan Immel |
| author_facet | Matthias Köck Michael Reggelin Stefan Immel |
| author_sort | Matthias Köck |
| collection | DOAJ |
| description | 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 (<i>J</i>) 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 (<b>1</b>), tetrabromostyloguanidine (<b>2</b>), 3,7-<i>epi</i>-massadine chloride (<b>3</b>), tubocurarine (<b>4</b>), and vincristine (<b>5</b>). Compounds <b>1</b>–<b>3</b> are marine natural products whereas <b>4</b> and <b>5</b> 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. |
| first_indexed | 2024-03-10T18:54:23Z |
| format | Article |
| id | doaj.art-86ecb56001e346558bdd5e0b46211442 |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T18:54:23Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-86ecb56001e346558bdd5e0b462114422023-11-20T04:52:09ZengMDPI AGMarine Drugs1660-33972020-06-0118633010.3390/md18060330The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural ProductsMatthias Köck0Michael Reggelin1Stefan Immel2Alfred-Wegener-Institut für Polar-und Meeresforschung in der Helmholtz-Gemeinschaft, Am Handelshafen 12, 27570 Bremerhaven, GermanyClemens-Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Alarich-Weiss-Straße 4, 64287 Darmstadt, GermanyClemens-Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Alarich-Weiss-Straße 4, 64287 Darmstadt, GermanyThe 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 (<i>J</i>) 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 (<b>1</b>), tetrabromostyloguanidine (<b>2</b>), 3,7-<i>epi</i>-massadine chloride (<b>3</b>), tubocurarine (<b>4</b>), and vincristine (<b>5</b>). Compounds <b>1</b>–<b>3</b> are marine natural products whereas <b>4</b> and <b>5</b> 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.https://www.mdpi.com/1660-3397/18/6/330chiralityconfigurational analysisdistance geometryNMR spectroscopyNOE dataresidual dipolar couplings |
| spellingShingle | Matthias Köck Michael Reggelin Stefan Immel The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products Marine Drugs chirality configurational analysis distance geometry NMR spectroscopy NOE data residual dipolar couplings |
| title | The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products |
| title_full | The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products |
| title_fullStr | The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products |
| title_full_unstemmed | The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products |
| title_short | The Advanced Floating Chirality Distance Geometry Approach―How Anisotropic NMR Parameters Can Support the Determination of the Relative Configuration of Natural Products |
| title_sort | advanced floating chirality distance geometry approach how anisotropic nmr parameters can support the determination of the relative configuration of natural products |
| topic | chirality configurational analysis distance geometry NMR spectroscopy NOE data residual dipolar couplings |
| url | https://www.mdpi.com/1660-3397/18/6/330 |
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