Angewandte Chemie International Edition · 2008 · 84 citations · 27 references
Natural SciencesBiochemistryChemistryBioisosterismDrug DiscoverySpectroscopyMonosaccharide StereochemistrySpectroscopy Of BiomoleculesAbsolute Configuration AssignmentAbsolute Configuration DeterminationCarbohydrate Stereochemistry DeterminationConfiguration Determination By Nuclear Magnetic Resonance SpectroscopyRelative Configuration DeterminationResidual Dipolar Coupling AnalysisResidual Dipolar CouplingsStereochemical Analysis By Nuclear Magnetic Resonance Spectroscopy
A new method based on NMR spectroscopy is introduced to determine the absolute configuration of natural compounds and has been successfully applied to sucro-neolambertellin. The method relies on the measurement of residual dipolar couplings (RDCs), which allow the absolute configuration of unknown stereocenters to be related with known stereocenters (see picture). The approach is used to determine the configuration of the D-threo-2,5-hexodiulofuranose moiety by relating it to α-D-glucose.
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The Xplor-NIH NMR molecular structure determination package
Charles D. Schwieters, John Kuszewski, Nico Tjandra et al. · Journal of Magnetic Resonance · 2003 · 2.4K citations
Life Sciences, Biophysics, Chemistry +10