Date of Award
Doctor of Philosophy
Daniel W. Armstrong
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.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu
Ling (Tom) Shi Xiao
Xiao, Ling (Tom) Shi, "Enantiomeric separations using macrocyclic glycopeptide based chiral stationary phases, an application and mechanism study " (2004). Retrospective Theses and Dissertations. 826.