Incorporation of 2′-deoxy-5-(trifluoromethyl)uridine and 5-cyano-2′-deoxyuridine into DNA

John C. Markley, Panadda Chirakul, Dina Sologub, Snorri Th Sigurdsson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)


In an attempt to synthesize DNA containing 2′-deoxy-5-(trifluoromethyl)uridine (1) using previously published protocols, we found that the trifluoromethyl group converted into a cyano group, resulting in DNA containing 5-cyano-2′-deoxyuridine (3). We show that nucleoside 1 can be incorporated into DNA using phosphoramidite 2 in combination with acetyl-protected deoxycytidine and phenoxyacetyl-protected purine phosphoramidites. Replacing thymidine in DNA with 1 caused a slight decrease in DNA duplex stability at pH 6.9.

Original languageEnglish
Pages (from-to)2453-2455
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Issue number18
Publication statusPublished - 17 Sept 2001

Bibliographical note

Funding Information:
We thank the National Institutes of Health (GM58914 and GM56947) for financial support, Dr. G. P. Drobny and E. A. Louie for helpful discussions, Dr. M. Sadilek for help with MS analyses and members of the Sigurdsson research group for critical reading of the manuscript.


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