Synthesis of nucleoside units possessing photoreactive diazirine groups on the major and minor groove faces

Abstract In this work, we developed and examined photoreactive nucleoside units, which are chemical probes to investigate the interaction between nucleic acids and proteins. Starting with 6-chloro-7-iodo-7-deazapurine derivative 5 , 7-(3-oxobutyl)-7-deazaadenosine derivative 8 was prepared via a palladium-catalyzed reaction with 3-buten-2-ol. Then, the carbonyl group of 8 was converted into a diazirinyl group to provide the desired Dia 7 C 7 A 3 . In a similar manner, Dia 2 A 4 was prepared from 2 to iodoadenosine derivative 11 . The resulting 3 and 4 were confirmed to form chemically active carbene species via photo-irradiation.