DOI

10.17077/etd.0i6x1vev

Document Type

Dissertation

Date of Degree

Summer 2018

Degree Name

PhD (Doctor of Philosophy)

Degree In

Chemistry

First Advisor

Gregory K. Friestad

First Committee Member

Leonard MacGillivray

Second Committee Member

James Gloer

Third Committee Member

Gary Small

Fourth Committee Member

Edward Gillan

Abstract

This thesis consists of two parts, both on synthetic chemistry with medicinal and biological relevance. Part one aims to develop methods for the preparation of quinazoline derivatives. A streamlined method for the preparation of 6-substituted-4-methyl-2-quinazolyl-guanidines and their respective amides has been presented here, using inexpensive and readily available starting materials such as para-bromoaniline, dicyandiamide (DCDA), and other reagents that are well-established for reactions such as Heck coupling, Suzuki coupling, and Ullman coupling reactions. In part two a novel methodology was developed for the specific incorporation of a masked N,O-acetal at the peptide bond between glycine and other amino acids including phenylalanine, alanine, valine, leucine, isoleucine, aspartate, glutamate, and the aromatic amino acids tyrosine and tryptophan. This methodology opens the door to linking a wide variety of derivatives, including carboxylic acids, to a specific peptide bond within a oligopeptide fragment. Such derivatives can be useful in the development of natural products containing these specific linkages or in the development of oligopeptides tagged at specific locations with a biodegradable and traceless linker useful in identifying and reacting with their peptide ligands.

Keywords

Quinazolines

Pages

xi, 242 pages

Bibliography

Includes bibliographical references (pages 139-146).

Comments

This thesis has been optimized for improved web viewing. If you require the original version, contact the University Archives at the University of Iowa: http://www.lib.uiowa.edu/sc/contact/

Copyright

Copyright © 2018 Sherif M. S. Ibrahim

Included in

Chemistry Commons

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