Synthesis of Novel 5-Aryl 2’-Deoxyuridine and 2’-Deoxycytidine Analogues

<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>

Name thesis:degree_name

Master of Science (M.S.)

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Biology

Year dc:date.available

2024

Author dc:creator

• Persaud, Kevin E.

Contributors dc:contributor

• Mahesh K. Lakshman
• Mark Pezzano
• Karen Hubbard

• Pyrimidine nucleoside analogous
• Cancer Biology
• Cell Biology
• Organic Chemistry

Repository record dc:identifier

https://academicworks.cuny.edu/cc_etds_theses/1176

OAI identifier oai:identifier

oai:academicworks.cuny.edu:cc_etds_theses-2263