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Synthesis And Spectroscopic Studies Of Substituted Pyrrolocytidines, Mckenry Charles

Electronic Thesis and Dissertation Repository

This thesis reports work in the area of modified nucleosides for potential use as molecular probes in nucleic acid chemistry. These heterocyclic base surrogates that are capable of canonical base pairing have use in the study of nucleic acid conformation, as reporters of the state of hybridization.^[1]

The synthesis of a 5-phenylpyrrolocytidine was attempted in order to compare its properties with its 6-substituted pyrrolocytidine counterpart. Unfortunately, the 5-substituted pyrrolocytidine was not achieved.

The synthesis of five nucleosides based on the pyrrolocytidine scaffold was reported. Their synthesis was achieved through the tandem Sonogashira/annulations reaction between 5-iodocytidine derivatives and …