S y n t h e s i s o f 7 -D e a z a p u r i n e D e r i v a t i v e s f r o m 5 -I o d o c y t o s i n eAbstract: Fluorescent bicyclic analogs of cytosine have been synthesized directly from derivatives of 5-iodocytosine by a onepot sequential Sonogashira cross-coupling and annulation with terminal alkynes. The spectral properties of these compounds depend on the identity of the alkyne. 7-Deazapurines synthesized from substituted phenylacetylenes possess greater fluorescence than those derived from alkyl substituted alkynes.
Peptide nucleic acid (PNA) presents a versatile scaffold for chemical modifications that may benefit its solubility and hybridization properties, conjugation chemistry, cell membrane permeability, and so forth. We have employed straightforward chemical methods for the synthesis of PNA monomers containing C5-or C6-modified pyrimidines.The C5-modified pyrimidines are based on 5-hydroxymethyl-uracil or cytosine, or are achieved by cross-coupling from the 5-iodonucleobase derivatives, while C6 modifications are accessed from 6-carboxyuracil (orotic acid). We have also developed an on-resin activation/conversion of uracil-containing PNA oligomers to N4-cytosine-containing derivatives.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.