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Lessor, Ralph Arthur 2014-12-15T23:18:03Z 2014-12-15T23:18:03Z 10000-01-01 1984 1984 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. Made available in DSpace on 2014-12-15T23:18:03Z (GMT). No. of bitstreams: 1 8409802.pdf: 2746649 bytes, checksum: fc2758e7ae8d2c64c047935e449c8f17 (MD5) Previous issue date: 1984 Embargo set by: Seth Robbins for item 70402 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 85 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984. http://hdl.handle.net/2142/70236 (UMI)AAI8409802 Chemistry, Organic Synthesis and Biological Evaluation of 2'-Deoxyribonucleotide Analogs text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.