NEW PHOTOREACTIVE N-4-SUBSTITUTED DCTP ANALOGS - PREPARATION, PHOTOCHEMICAL CHARACTERISTICS, AND SUBSTRATE PROPERTIES IN HIV-1 REVERSE TRANSCRIPTASE-CATALYZED DNA-SYNTHESIS

Photochemical characteristics and substrate properties of four newly s ynthesized dCTP analogues: N-4-[2-(2-nitro-5-azidobenzoylamino)ethyl]- , afluorobenzylideneaminooxymethylcarbamoyl)ethyl]-, (4-azidotetrafluo robenzylideneaminooxy)butyloxy]-, and N-4-[4-(4-azidotetrafluorobenzyl idene hydrazinocarbonyl)butylcarbamoyl]-, and uorobenzylideneaminooxy) butyloxy]-2'-deoxycytidine 5'-triphosphates as well as those of the ea rlier described N-4-[2-(4-azidotetrafluorobenzoylamino)ethyl]- and afl uorobenzoylamino)-1-propenyl)]-2'-deoxycytidine 5'-triphosphates were compared. When being irradiated with UV light at a wavelength of 303-3 13 nm, the new analogues demonstrated greater than 10-fold higher phot oactivity as compared with the old compounds. The first three new comp ounds were utilized by HIV-1 reverse transcriptase as dCTP and dTTP, w hile the last derivative was recognized only as dTTP. Once incorporate d into the primer 3'-terminus, none of the analogues synthesized termi nated further primer elongation with natural triphosphates.