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DIFLUOROMETHYLPHOSPHONATE: A VERSATILE REAGENT FOR
SYNTHESIS OF NOVEL ISOPOLAR AND BIOISOSTERIC NUCLEOTIDE
ANALOGUES
by
Mikhail Zibinsky
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 Mikhail Zibinsky
Object Description
| Title | Difluoromethylphosphonate: a versatile reagent for synthesis of novel isopolar and bioisosteric nucleotide analogues |
| Author | Zibinsky, Mikhail |
| Author email | zibinsky@usc.edu; zibinsky@gmail.com |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2009-06-15 |
| Date submitted | 2009 |
| Restricted until | Unrestricted |
| Date published | 2009-08-05 |
| Advisor (committee chair) | Prakash, G. K. Surya |
| Advisor (committee member) |
Olah, George A. Shing, Katherine |
| Abstract | This dissertation describes the development of novel nonhydrolizable deoxynucleotide analogues toolkit based on substitution of oxygen atoms for CF2 groups in triphosphate group. Synthesis of unknown bis(difluoromethylene)triphosphonic acid is also reported.; New methodologies for nucleophilic transfer of difluoromethyl- and difluoromethylene groups were developed based on utilizing deifluoromethylphosphonate as the synthetic analog of those functional groups.; Chapter 1 summarizes current state of the art of triphoshate modified nucleotide analogues field with the emphasis on their preparation. Chapter 2 describes an efficient synthesis of previously unknown bis(difluoromethylene)triphosphonic acid and related salts. Chapter 3 deals with the synthesis of deoxynucleotide analogues and their biological applications. Chapter 4 expounds new phosphonate-based procedures of [CF2H-] and [CF22-] tansfer reactions. |
| Keyword | nucleotide; triphosphate; triphosphonate; phosphorous; DNA; non-hydrolyzable |
| 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-m2481 |
| Rights | Zibinsky, Mikhail |
| 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-Zibinsky-2703 |
| Archival file | uscthesesreloadpub_Volume26/etd-Zibinsky-2703.pdf |
Description
| Title | Page 1 |
| Full text | DIFLUOROMETHYLPHOSPHONATE: A VERSATILE REAGENT FOR SYNTHESIS OF NOVEL ISOPOLAR AND BIOISOSTERIC NUCLEOTIDE ANALOGUES by Mikhail Zibinsky 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 Mikhail Zibinsky |
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