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BISPHOSPHONATES FOR MODIFIED NUCLEOTIDE SYNTHESIS AND
RELATED CHEMISTRY
by
Rehana Ismail
A Dissertation Presented to the
FACULTY OF THE GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFORNIA
In Partial Fulfillment of the
Requirements for the Degree
DOCTOR OF PHILOSOPHY
(CHEMISTRY)
August 2009
Copyright 2009 Rehana Ismail
Object Description
| Title | Bisphosphonates for modified nucleotide synthesis and related chemistry |
| Author | Ismail, Rehana |
| Author email | rismail@usc.edu; reha.ismail@gmail.com |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2009-06-24 |
| Date submitted | 2009 |
| Restricted until | Unrestricted |
| Date published | 2009-07-29 |
| Advisor (committee chair) | Prakash, G. K. Surya |
| Advisor (committee member) |
Olah, G. A. Shing, Kathrine Rasul, Golam |
| Abstract | This dissertation explores the field of organophosphorus chemistry. Phosphorus plays a major role in medicinal and natural product chemistry, which is the inspiration for the majority of the work presented in this dissertation.; The first chapter is a short description of the vast field of organophosphorus chemistry. Phosphorus holds a unique place in the periodic table and its wide spread applications in various fields are presented. Short descriptions of the most important applications are explored, with special emphasis on phosphorus based reagents and biological relevant molecules.; Chapter 2 describes the one pot synthesis of Kabachnik-Fields reaction for fluorinated α-aminophosphosphonates, amino acid analogs, with gallium triflate. Some mechanistic aspects are explored with respect to fluorinated imines and aminals.; Chapter 3 deals with various pyrophosphonic acid analogs of bisphosphonic acids,triphosphate analogs. The pKa's of 3,3,3 -trifluoro-2,2 -dihydroxypropylphosphonic acid, a pyrophosphonic acid analog are evaluated. The synthesis of modified nucleotide analog with 3,3,3 -trifluoro-2,2 -dihydroxypropylphosphonic acid is described.; Chapter 4 presents a simple and mild reagent for the a-chlorination and a-bromination of ketones with acidic a-hydrogens. TMS-X (where X= Br,or Cl) and KNO3 salt is used to carry out a-bromination and a-chlorination with good conversion and selectivity. |
| Keyword | bisphosphonates; modified nucleotides; phosphorus |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Provenance | Electronically uploaded by the author |
| Type | texts |
| Legacy record ID | usctheses-m2413 |
| Rights | Ismail, Rehana |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Ismail-3150 |
| Archival file | uscthesesreloadpub_Volume23/etd-Ismail-3150.pdf |
Description
| Title | Page 1 |
| Full text | BISPHOSPHONATES FOR MODIFIED NUCLEOTIDE SYNTHESIS AND RELATED CHEMISTRY by Rehana Ismail A Dissertation Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY (CHEMISTRY) August 2009 Copyright 2009 Rehana Ismail |
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