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Access Type

WSU Access

Date of Award

January 2011

Degree Type

Dissertation

Degree Name

Ph.D.

Department

Chemistry

First Advisor

JEREMY J. KODANKO

Abstract

Three research areas pertaining to this dissertation, (i) synthesis strategies of peptide-ligand conjugates, (ii) their applications and (iii) chemistry of ferryls were surveyed in the introduction chapter. Next, the divergent and dual divergent strategies for the synthesis of non-heme ligand-peptide conjugates were developed. Using these strategies various peptide-ligand conjugates were synthesized via solution as well as solid phase synthesis. The scope and the functional group compatibility of these strategies were also established. The utility of the dual divergent strategy has been demonstrated by synthesizing a small library of metal-binding LHRH analogues. This work showcased the ability of the dual divergent strategy to rapidly construct the diverse array of ligand structures. In another application, the synthesis and characterization of the first ferryl-peptide conjugate was presented. In this work the reactivity and the mechanistic study for this ferryl-peptide conjugate were also described. From the mechanistic studies it has been proven that the remote benzyl group controls the stability of ferryl-peptide conjugate via an intramolecular hydrogen atom transfer mechanism.