Briefly, the following report details a synthetic route to prepare 5-phenyl-2’-deoxycytidine analogues. This multistep synthesis began with silyl protection of the 3’- and 5’-hydroxyl groups of 5-iodo-2’-deoxyuridine. Next, the installation of a phenyl ring at the C5 position of the nucleobase via a Suzuki-Miyaura cross-coupling reaction, yielding 5-phenyl-2’-deoxyuridine (5-PdU). After that, modification of the obtained 5-PdU at the C4 position was performed with benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, a peptide-coupling agent) and a base (cesium carbonate) to activate the amide group of the uridine nucleobase for subsequent displacement with a variety of amines. Modification of the C4 position resulted in protected 5-phenyl-2’-deoxycytidine (5-PdC) derivatives. To complete the synthesis, the 3’- and 5’-silyl groups were removed by a fluoride source (n-tetrabutylammonium fluoride, TBAF) to generate unprotected 5-PdC analogues. Additionally, potential enzymes that may recognize the 5-PdC analogues and a proposed evaluation of the 5-PdC analogues’ biological properties have been presented.
","abstract_html":"<p>Briefly, the following report details a synthetic route to prepare 5-phenyl-2’-deoxycytidine analogues. This multistep synthesis began with silyl protection of the 3’- and 5’-hydroxyl groups of 5-iodo-2’-deoxyuridine. Next, the installation of a phenyl ring at the C5 position of the nucleobase via a Suzuki-Miyaura cross-coupling reaction, yielding 5-phenyl-2’-deoxyuridine (5-PdU). After that, modification of the obtained 5-PdU at the C4 position was performed with benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, a peptide-coupling agent) and a base (cesium carbonate) to activate the amide group of the uridine nucleobase for subsequent displacement with a variety of amines. Modification of the C4 position resulted in protected 5-phenyl-2’-deoxycytidine (5-PdC) derivatives. To complete the synthesis, the 3’- and 5’-silyl groups were removed by a fluoride source (<em>n</em>-tetrabutylammonium fluoride, TBAF) to generate unprotected 5-PdC analogues. Additionally, potential enzymes that may recognize the 5-PdC analogues and a proposed evaluation of the 5-PdC analogues’ biological properties have been presented.</p>","abstract_has_math":false,"creators":["Persaud, Kevin E."],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis","degree_discipline":"Biology","degree_department":null,"school":null,"contributors":["Mahesh K. Lakshman","Mark Pezzano","Karen Hubbard"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2024,"date_issued":"2024-01-01T08:00:00Z","date_published":"2024-01-01T08:00:00Z","updated_at":"2026-07-24T01:58:07Z","subjects":["Pyrimidine nucleoside analogous","Cancer Biology","Cell Biology","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://academicworks.cuny.edu/cc_etds_theses/1176","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Mahesh K. Lakshman","Mark Pezzano","Karen Hubbard"]},{"key":"dc:creator","label":"Author","values":["Persaud, Kevin E."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2025-08-18T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Biology"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Pyrimidine nucleoside analogous","Cancer Biology","Cell Biology","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://academicworks.cuny.edu/cc_etds_theses/1176"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Briefly, the following report details a synthetic route to prepare 5-phenyl-2’-deoxycytidine analogues. This multistep synthesis began with silyl protection of the 3’- and 5’-hydroxyl groups of 5-iodo-2’-deoxyuridine. Next, the installation of a phenyl ring at the C5 position of the nucleobase via a Suzuki-Miyaura cross-coupling reaction, yielding 5-phenyl-2’-deoxyuridine (5-PdU). After that, modification of the obtained 5-PdU at the C4 position was performed with benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, a peptide-coupling agent) and a base (cesium carbonate) to activate the amide group of the uridine nucleobase for subsequent displacement with a variety of amines. Modification of the C4 position resulted in protected 5-phenyl-2’-deoxycytidine (5-PdC) derivatives. To complete the synthesis, the 3’- and 5’-silyl groups were removed by a fluoride source (n-tetrabutylammonium fluoride, TBAF) to generate unprotected 5-PdC analogues. Additionally, potential enzymes that may recognize the 5-PdC analogues and a proposed evaluation of the 5-PdC analogues’ biological properties have been presented.
"]},{"key":"dc:title","label":"Title","values":["Synthesis of Novel 5-Aryl 2’-Deoxyuridine and 2’-Deoxycytidine Analogues"]}]}],"canonical_facts":{"dc:contributor":["Mahesh K. Lakshman","Mark Pezzano","Karen Hubbard"],"dc:creator":["Persaud, Kevin E."],"dc:date.available":["2025-08-18T07:00:00Z"],"dc:description.abstract":["Briefly, the following report details a synthetic route to prepare 5-phenyl-2’-deoxycytidine analogues. This multistep synthesis began with silyl protection of the 3’- and 5’-hydroxyl groups of 5-iodo-2’-deoxyuridine. Next, the installation of a phenyl ring at the C5 position of the nucleobase via a Suzuki-Miyaura cross-coupling reaction, yielding 5-phenyl-2’-deoxyuridine (5-PdU). After that, modification of the obtained 5-PdU at the C4 position was performed with benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, a peptide-coupling agent) and a base (cesium carbonate) to activate the amide group of the uridine nucleobase for subsequent displacement with a variety of amines. Modification of the C4 position resulted in protected 5-phenyl-2’-deoxycytidine (5-PdC) derivatives. To complete the synthesis, the 3’- and 5’-silyl groups were removed by a fluoride source (n-tetrabutylammonium fluoride, TBAF) to generate unprotected 5-PdC analogues. Additionally, potential enzymes that may recognize the 5-PdC analogues and a proposed evaluation of the 5-PdC analogues’ biological properties have been presented.
"],"dc:identifier":["https://academicworks.cuny.edu/cc_etds_theses/1176"],"dc:subject":["Pyrimidine nucleoside analogous","Cancer Biology","Cell Biology","Organic Chemistry"],"dc:title":["Synthesis of Novel 5-Aryl 2’-Deoxyuridine and 2’-Deoxycytidine Analogues"],"thesis:degree_discipline":["Biology"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T01:58:07Z"}