Nath, Nilamoni ; Fuentes-Monteverde, Juan Carlos ; Pech-Puch, Dawrin ; Rodríguez, Jaime ; Jiménez, Carlos ; Noll, Markus ; Kreiter, Alexander ; Reggelin, Michael ; Navarro-Vázquez, Armando ; Griesinger, Christian (2024)
Relative configuration of micrograms of natural compounds using proton residual chemical shift anisotropy.
In: Nature Communications, 2020, 11 (1)
doi: 10.26083/tuprints-00024031
Artikel, Zweitveröffentlichung, Verlagsversion
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Kurzbeschreibung (Abstract)
3D molecular structure determination is a challenge for organic compounds or natural products available in minute amounts. Proton/proton and proton/carbon correlations yield the constitution. J couplings and NOEs oftentimes supported by one-bond ¹H,¹³C residual dipolar couplings (RDCs) or by ¹³C residual chemical shift anisotropies (RCSAs) provide the relative configuration. However, these RDCs or carbon RCSAs rely on 1% natural abundance of ¹³C preventing their use for compounds available only in quantities of a few 10’s of µgs. By contrast, ¹H RCSAs provide similar information on spatial orientation of structural moieties within a molecule, while using the abundant ¹H spin. Herein, ¹H RCSAs are accurately measured using constrained aligning gels or liquid crystals and applied to the 3D structural determination of molecules with varying complexities. Even more, deuterated alignment media allow the elucidation of the relative configuration of around 35 µg of a briarane compound isolated from Briareum asbestinum.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 2024 |
| Autor(en): | Nath, Nilamoni ; Fuentes-Monteverde, Juan Carlos ; Pech-Puch, Dawrin ; Rodríguez, Jaime ; Jiménez, Carlos ; Noll, Markus ; Kreiter, Alexander ; Reggelin, Michael ; Navarro-Vázquez, Armando ; Griesinger, Christian |
| Art des Eintrags: | Zweitveröffentlichung |
| Titel: | Relative configuration of micrograms of natural compounds using proton residual chemical shift anisotropy |
| Sprache: | Englisch |
| Publikationsjahr: | 25 September 2024 |
| Ort: | Darmstadt |
| Publikationsdatum der Erstveröffentlichung: | 1 September 2020 |
| Ort der Erstveröffentlichung: | London |
| Verlag: | Springer Nature |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Nature Communications |
| Jahrgang/Volume einer Zeitschrift: | 11 |
| (Heft-)Nummer: | 1 |
| Kollation: | 9 Seiten |
| DOI: | 10.26083/tuprints-00024031 |
| URL / URN: | https://tuprints.ulb.tu-darmstadt.de/24031 |
| Zugehörige Links: | |
| Herkunft: | Zweitveröffentlichung DeepGreen |
| Kurzbeschreibung (Abstract): | 3D molecular structure determination is a challenge for organic compounds or natural products available in minute amounts. Proton/proton and proton/carbon correlations yield the constitution. J couplings and NOEs oftentimes supported by one-bond ¹H,¹³C residual dipolar couplings (RDCs) or by ¹³C residual chemical shift anisotropies (RCSAs) provide the relative configuration. However, these RDCs or carbon RCSAs rely on 1% natural abundance of ¹³C preventing their use for compounds available only in quantities of a few 10’s of µgs. By contrast, ¹H RCSAs provide similar information on spatial orientation of structural moieties within a molecule, while using the abundant ¹H spin. Herein, ¹H RCSAs are accurately measured using constrained aligning gels or liquid crystals and applied to the 3D structural determination of molecules with varying complexities. Even more, deuterated alignment media allow the elucidation of the relative configuration of around 35 µg of a briarane compound isolated from Briareum asbestinum. |
| Freie Schlagworte: | Marine chemistry, Solution-state NMR, Structure elucidation |
| ID-Nummer: | Artikel-ID: 4372 |
| Status: | Verlagsversion |
| URN: | urn:nbn:de:tuda-tuprints-240310 |
| Zusätzliche Informationen: | "The original version of the Supplementary Information associated with this Article contained errors in Supplementary Fig. 9a and on page 7. In both cases, chemical formula of the liquid crystalline medium was drawn incorrectly. The HTML has been updated to include a corrected version of the Supplementary Information; the original incorrect versions of these Figs. can be found as Supplementary Information associated with this Correction." |
| Sachgruppe der Dewey Dezimalklassifikatin (DDC): | 500 Naturwissenschaften und Mathematik > 540 Chemie 500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie |
| Fachbereich(e)/-gebiet(e): | 07 Fachbereich Chemie 07 Fachbereich Chemie > Clemens-Schöpf-Institut 07 Fachbereich Chemie > Clemens-Schöpf-Institut > Fachgebiet Organische Chemie |
| Hinterlegungsdatum: | 25 Sep 2024 11:33 |
| Letzte Änderung: | 26 Sep 2024 07:34 |
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| Suche nach Titel in: | TUfind oder in Google |
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