RDC-Enhanced NMR Spectroscopy in Structure Elucidation of Sucro-Neolambertellin†
This work was supported by the Max Planck Society, the DFG (GRK 782), and the Fonds der Chemischen Industrie. Part of this work was also supported by a grant-in-aid for scientific research (no. 17580090) from the Ministry of Education, Culture, Sports, Science and Technology of Japan. We also thank the Suntory Institute for Bioorganic Research for the SUNBOR Grant. We thank Prof. Jun Kawabata and Dr. Eri Fukushi of Hokkaido University for mass spectrometry measurements, and Dr. Edward d′Auvergne for insightful discussions and careful reading.
Graphical Abstract
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.
