Date of Award

Spring 5-17-2013

Degree Type

Dissertation

Degree Name

Ph.D.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Dr Branko S Jursic

Second Advisor

Dr. Mark Trudell

Third Advisor

Dr Ed Steven

Fourth Advisor

Dr Lee Roy Morgan

Abstract

Invasive fungal infections are a major threat to immune-compromised patients. There is a critical need to develop new antifungal agents because of increasing resistance to the common antifungal drugs.

In the first part of this dissertation, methods for preparation of novel barbiturate saponin as antifungals and their biological activities would be described. Barbiturates and steroidal saponins have shown remarkable antifungal activity in the biological assays. Therefore, attempts were directed to combine the barbiturate with the steroid to give novel antifungal agents. The need for extensive SAR studies and to better understand these compounds efforts were directed to synthesize novel saponin barbiturates.

Glycosylation of barbiturates was achieved under basic conditions to synthesize mono and disaccharide barbiturates. Saccharide molecules were directly introduced into the barbiturate without requiring protection and deprotection of saccharides. Efficient methods were developed for synthesis of 3β derivatized steroid derivatives containing ether, carbonate, ester and carbamate linker. Synthesized mono and disaccharide barbiturates were incorporated into the steroidal skeleton to give the novel antifungal agents. Several reaction conditions were explored to give the best yield under the most efficient reaction conditions. However, a better understanding and extensive SAR study needs to be done in order to develop more promising and potent antifungal compounds.

The second part of this dissertation describes the progress towards monocysteine metal complex synthesis and their biological activities. In this attempt, several protection deprotection strategies were explored and some novel protective groups were designed for peptide 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.

Available for download on Thursday, May 17, 2018

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