Model-Free Approach for the Configurational Analysis of Marine Natural Products
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 <i>J</i> couplings as well as anisotropic parameters. The combined d...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-05-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/19/6/283 |
| _version_ | 1797531767034347520 |
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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 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 <i>J</i> 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 <i>cis</i>-palau’amine derivatives <b>1a</b> and <b>1b</b>, tetrabromostyloguanidine (<b>1c</b>), plakilactone H (<b>2</b>), and manzamine A (<b>3</b>). 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. |
| first_indexed | 2024-03-10T10:49:25Z |
| format | Article |
| id | doaj.art-0bd4b18e8ddf4ddeb5c16ae671efe85f |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T10:49:25Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-0bd4b18e8ddf4ddeb5c16ae671efe85f2023-11-21T22:21:12ZengMDPI AGMarine Drugs1660-33972021-05-0119628310.3390/md19060283Model-Free Approach for the Configurational Analysis of Marine Natural ProductsMatthias Köck0Michael Reggelin1Stefan Immel2Alfred Wegener Institute, Helmholtz Centre for Polar and Marine Research, Am Handelshafen 12, 27570 Bremerhaven, GermanyClemens-Schöpf-Institute for Organic Chemistry and Biochemistry, Technical University of Darmstadt, Alarich-Weiss-Straße 4, 64287 Darmstadt, GermanyClemens-Schöpf-Institute for Organic Chemistry and Biochemistry, Technical University of Darmstadt, Alarich-Weiss-Straße 4, 64287 Darmstadt, GermanyThe 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 <i>J</i> 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 <i>cis</i>-palau’amine derivatives <b>1a</b> and <b>1b</b>, tetrabromostyloguanidine (<b>1c</b>), plakilactone H (<b>2</b>), and manzamine A (<b>3</b>). 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.https://www.mdpi.com/1660-3397/19/6/283configurational analysisdistance geometrydistance bounds driven dynamicsNMR spectroscopyNOE data |
| spellingShingle | Matthias Köck Michael Reggelin Stefan Immel Model-Free Approach for the Configurational Analysis of Marine Natural Products Marine Drugs configurational analysis distance geometry distance bounds driven dynamics NMR spectroscopy NOE data |
| title | Model-Free Approach for the Configurational Analysis of Marine Natural Products |
| title_full | Model-Free Approach for the Configurational Analysis of Marine Natural Products |
| title_fullStr | Model-Free Approach for the Configurational Analysis of Marine Natural Products |
| title_full_unstemmed | Model-Free Approach for the Configurational Analysis of Marine Natural Products |
| title_short | Model-Free Approach for the Configurational Analysis of Marine Natural Products |
| title_sort | model free approach for the configurational analysis of marine natural products |
| topic | configurational analysis distance geometry distance bounds driven dynamics NMR spectroscopy NOE data |
| url | https://www.mdpi.com/1660-3397/19/6/283 |
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