Difluoromethylphosphonate: A versatile reagent for synthesis of novel isopolar and bioisosteric nucleotide analogues
by Zibinsky, Mikhail, Ph.D., UNIVERSITY OF SOUTHERN CALIFORNIA, 2009, 227 pages; 3368731

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 unkown bis(difluoromethylene)triphosphonic acid and related salts.

Chapter 3 deals with the synthesis of deoxynucleotide analogues and their biological aplications.

Chapter 4 expounds new phosphonate-based procedures of [CF2H -] and [CF22-] transfer reactions.

 
AdvisersG. K. Surya Prakash; George A. Olah
SchoolUNIVERSITY OF SOUTHERN CALIFORNIA
SourceDAI/B 70-08, p. , Sep 2009
Source TypeDissertation
SubjectsBiochemistry; Organic chemistry
Publication Number3368731
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