{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70236"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70236","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthesis and Biological Evaluation of 2'-Deoxyribonucleotide Analogs","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Lessor, Ralph Arthur"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-15T23:18:03Z","date_published":"2014-12-15T23:18:03Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8409802"],"render_values":[{"text":"(UMI)AAI8409802","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70236","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Lessor, Ralph Arthur"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T23:18:03Z","10000-01-01","1984"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/70236","(UMI)AAI8409802"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["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). 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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). 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