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.
|Number of pages||3|
|Journal||Bioorganic and Medicinal Chemistry Letters|
|Publication status||Published - 17 Sept 2001|
Bibliographical noteFunding 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.