Date of Award

8-10-2005

Degree Type

Dissertation

Degree Name

Ph.D.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Jursic, Branko

Second Advisor

Wang, Guijun

Third Advisor

Trudell, Mark

Fourth Advisor

Tarr, Matthew

Abstract

There is a strong market demand for enantiomerically pure drugs. One solution to this problem is to develop a simple methodology for transferring synthetically designed racemic drugs into optically pure ones. Many synthetic drugs are by nature amides, therefore, amino acid based models for transformation of racemates into optically pure compounds were selected for this study. Formation of self-assembly molecular aggregates of properly modified amino acids was observed with and without the presence of cyclodextrins. Cyclodextrin assisted formation of polymer-like self-assemblies and enantiomeric resolution of these amino acids were studied using 1D and 2D NMR spectroscopy, EleacroSpray Ionization Mass Spectroscopy (ESIMS), Matrix- Assisted Laser Desorption Ionization Time-of-Flight Mass Spectroscopy (MALDI-TOF-MS). The role of p-p stacking interaction between aromatic moieties in enantiomeric resolution was demonstrated by calculating association constants of this host-guest system. Dolabellane diterpenoids share the unique feature of a trans-bicyclo[9.3.0]tetradecane and most of them express antimicrobial, antitumor and antiviral activities. They are primarily obtained from marine resources. Dolabellane diterpenoid B was isolated from the Okinawan soft coral of the genus Clavularia by Iguchi and co-workers. Current efforts toward the synthesis of dolabellane diterpenoid B is discussed along with the plans for completion of its synthesis.

Rights

The University of New Orleans and its agents retain the non-exclusive license to archive and make accessible this dissertation or thesis in whole or in part in all forms of media, now or hereafter known. The author retains all other ownership rights to the copyright of the thesis or dissertation.

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