Degree Type

Dissertation

Date of Award

2004

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

Daniel W. Armstrong

Abstract

The purpose of this dissertation was to further investigate the mechanism by which macrocyclic glycopeptides are able to separate enantiomers and to try to develop and expand their application in high performance liquid chromatography (HPLC) and other related separation techniques. A unique application of enantiomeric separations for chiral sulfoxides using macrocyclic glycopeptide chiral stationary phases (CSPs) was first demonstrated. Furthermore, another successful enantiomeric separation of a series of biologically active racemic analogues of dihydrofurocoumarin was done using this class of CSPs. The macrocyclic glycopeptides proved to be exceptionally selective for many classes of chiral compounds. Enantiomeric recognition mechanism was discussed and investigated. The last part of this dissertation presented an absolute configuration determination approach using exciton coupling chirality method. This method was extended as a general method for determination of the absolute configuration of dihydrofuroangelicins bearing a variety of C-8 substituted double bonds, synthesized in the racemic form and resolved through enantioselective chromatography.

DOI

https://doi.org/10.31274/rtd-180813-142

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu

Copyright Owner

Ling (Tom) Shi Xiao

Language

en

Proquest ID

AAI3136359

File Format

application/pdf

File Size

217 pages

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