title: Incorporation of 2'-deoxy-5-(trifluoromethyl)uridine and 5-cyano-2'-deoxyuridine into DNA.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Washington, Seattle, 98195-1700, USA.
authors.forename: J C
authors.initials: JC
authors.lastname: Markley
authors.forename: P
authors.initials: P
authors.lastname: Chirakul
authors.forename: D
authors.initials: D
authors.lastname: Sologub
authors.forename: S T
authors.initials: ST
authors.lastname: Sigurdsson
mesh_terms: D001671:Biochemistry / Q000379:methods*; D004247:DNA / Q000737:chemistry*; D003857:Deoxyuridine / Q000031:analogs & derivatives / Q000737:chemistry; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D014271:Trifluridine
chemical_list: C448390:5-cyano-2'-deoxyuridine; D009692:Nucleic Acid Heteroduplexes; D004247:DNA; D014271:Trifluridine; D003857:Deoxyuridine