Relative configuration of micrograms of natural compounds using proton residual chemical shift anisotropy

Nilamoni Nath, Juan Carlos Fuentes-Monteverde, Dawrin Pech-Puch, Jaime Rodríguez, Carlos Jiménez, Markus Noll, Alexander Kreiter, Michael Reggelin, Armando Navarro-Vázquez and Christian Griesinger ()
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Nilamoni Nath: NMR based Structural Biology, MPI for Biophysical Chemistry
Juan Carlos Fuentes-Monteverde: NMR based Structural Biology, MPI for Biophysical Chemistry
Dawrin Pech-Puch: Universidade da Coruña
Jaime Rodríguez: Universidade da Coruña
Carlos Jiménez: Universidade da Coruña
Markus Noll: Technical University of Darmstadt
Alexander Kreiter: Technical University of Darmstadt
Michael Reggelin: Technical University of Darmstadt
Armando Navarro-Vázquez: CCEN, Universidade Federal de Pernambuco, Cidade Universitária
Christian Griesinger: NMR based Structural Biology, MPI for Biophysical Chemistry

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-18093-5

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