Synthetic Nucleoside and Nucleotides. XXXIV. Photoaffinity Labeling of HIV Reverse Transcriptase: Synthesis and Utilization of 2′,3′-Dideoxy Uridylate Analogs Bearing Aryl(trifluor0methyl)-Diazirine Moiety

In order to develop a photoaffinity labeling reagent for HIV-1 reverse transcriptase, a 2′,3′-dideoxyUTP analog bearing a photo-reactive group at the 5-position of the uracil ring, 2′,3′-dideoxy-E-5-[4-[3-(trifluoromethyl)-3Hdiazirin-3-yl]styryl]-UTP, was designed and synthesized. This photo-reactive analog could preferentially bind to the 66 kDa subunit of the p66/p51 heterodimeric HIV-1 reverse transcriptase under irradiation by near-ultraviolet light (365 nm).