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Title:Synthesis and Biological Evaluation of 2'-Deoxyribonucleotide Analogs
Author(s):Lessor, Ralph Arthur
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:Two new methods for the synthesis of 2'-deoxyribonucleosides have been developed. The first involves regioselective reductive deoxygenation of a suitably derivatized ribonucleoside. Tri-n-butyltin hydride reduction of a 2'-thiobenzoate derivative affords the desired 2'-deoxyribonucleoside in good yield. The second method for 2'-deoxyribonucleoside synthesis involves the stereoselective coupling of a derivatized 2-deoxyribofuranosyl bromide with heterocycles in the presence of silver tetrafluoroborate. These methods have been applied to the synthesis of 2'-deoxy-lin-benzoadenosine, a fluorescent deoxyribonucleotide analog. The analog was converted into the corresponding 5'-mono-, di-, and triphosphate derivatives. The diphosphate was found to be a substrate for phosphorylation by pyruvate kinase, and the triphosphate was found to be an acceptable replacement for 2'-deoxyadenosine-5'-triphosphate in DNA nick translation by E. coli DNA polymerase I.
Issue Date:1984
Type:Text
Description:85 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984.
URI:http://hdl.handle.net/2142/70236
Other Identifier(s):(UMI)AAI8409802
Date Available in IDEALS:2014-12-15
Date Deposited:1984


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