Residual Dipolar Couplings in Structure Determination of Natural Products

Abstract

The determination of natural products stereochemistry remains a formidable task. Residual dipolar couplings (RDCs) induced by anisotropic media are a powerful tool for determination of the stereochemistry of organic molecule in solution. This review will provide a short introduction on RDCs-based methodology for the structural elucidation of natural products. Special attention is given to the current availability of alignment media in organic solvents. The applications of RDCs for structural analysis of some examples of natural products were discussed and summarized.Graphical AbstractThis review provides a short introduction on RDCs-based methodology for the structural elucidation of natural products. Special attention is given to the current availability of alignment media in organic solvents. The applications of RDCs for structural analysis of some examples of natural products were discussed and summarized.

Single experiment measurement of residual dipolar couplings in aqueous solution using a biphasic bisperylene imide chromonic liquid crystal

“…NMR in weakly aligned media has become a firmly established tool for structural elucidation of organic compounds. [1][2][3] Although most applications to structural elucidation problems involved the use of residual dipolar couplings (RDCs), [4,5] mostly one-bond proton-carbon 1 D CH ones, residual chemical shift anisotropies (RCSAs), [6,7] and even 2 H residual quadrupolar couplings (RQCs) [8] have come recently into play.…”

Computationally-assisted discovery and structure elucidation of natural products

“…The chemical shift tensor information necessary for RCSA analysis can be obtained using density functional theory (DFT) calculations. Several reviews on the use of RDC and RCSA for the determination of relative configuration of small organic molecules have been published [27, 32–37]. More importantly, a protocol on the use of anisotropic NMR parameters for the structure elucidation of small organic compounds has recently become available [38].…”

Design and applications of lanthanide chelating tags for pseudocontact shift NMR spectroscopy with biomacromolecules

“…of a protein-protein complex for which the structures of the individual subunits have been determined previously by X-ray crystallography. A more exotic application of RDCs includes the determination of the stereochemistry of natural products [109]. Besides the use of RDCs for the structure determination of proteins, also the helix curvature, subunit or domain orientation and stoichiometry of homomultimeric nucleic acid complexes was investigated [110].…”