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

Abstract

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).

(1) Part XXXIII of this series: Kawaguchi, T.; Sakairi, H.; Kimura, S.; Yamaguchi, T.; Saneyoshi, M. Chem. Pharm. Bull. 1995, 43, 501–504.

^†This paper is dedicated to Dr. Yoshihisa Mizuno on occasion of his 75th birthday.

Notes

(1) Part XXXIII of this series: Kawaguchi, T.; Sakairi, H.; Kimura, S.; Yamaguchi, T.; Saneyoshi, M. Chem. Pharm. Bull. 1995, 43, 501–504.

^†This paper is dedicated to Dr. Yoshihisa Mizuno on occasion of his 75th birthday.