Conformational studies of carbohydrates and carbohydrate-containing molecules

Author

Karen Terry Welch, University of Tennessee

Date of Award

12-2002

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

David C. Baker

Abstract

In this dissertation, the conformations of carbohydrates and carbohydratecontaining molecules were explored for two types of compounds using NIVIR and molecular modeling techniques. The NMR studies provided data about molecular conformation, while the molecular models provided scaffolds for interpreting the physical data. Anthocyanins from Daucus carota bearing various acyl groups were studied in order to elucidate their conformations in aqueous solution. The anthocyanins studied have the general structure 3-0-{(6-O-acyl)-B-D-glucopyranosyl-(1—>6)-[B-Dxylopyranosyl-(l—>2)]-B-D-galactopyranosyl}cyanidin. The persistence of the red color of these compounds was shown to be influenced by the chemical structure of the attached acyl group. The comparison of the 1D and 2D NMR spectra of these compounds, as well as related monoacylated anthocyanins in methanol, revealed trends among all of the compounds that were indicative of molecular conformation.

Recommended Citation

Welch, Karen Terry, "Conformational studies of carbohydrates and carbohydrate-containing molecules. " PhD diss., University of Tennessee, 2002.
https://trace.tennessee.edu/utk_graddiss/6329