Enantiomeric separations using macrocyclic glycopeptide based chiral stationary phases, an application and mechanism study
Date
Authors
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
Altmetrics
Authors
Research Projects
Organizational Units
The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
History
The Department of Chemistry was founded in 1880.
Dates of Existence
1880-present
Related Units
- College of Liberal Arts and Sciences (parent college)
Journal Issue
Is Version Of
Versions
Series
Department
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.