title: Halogenation of tubercidin by N-halosuccinimides. A direct route to 5-bromotubercidin, a reversible inhibitor of RNA synthesis in eukaryotic cells.
abstract: Tubercidin may be directly brominated by reaction with N-bromosuccinimide in DMF to give 5-bromotubercidin, a reversible inhibitor of RNA synthesis. When buffered with potassium acetate the major product is 6-bromotubercidin. 5,6-Dibromotubercidin is formed in minor amounts under both conditions. N-Chlorosuccinimide and tubercidin give 5-chlorotubercidin and 5,6-dichlorotubercidin.
mesh_terms: D001974:Bromosuccinimide; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D012313:RNA / Q000037:antagonists & inhibitors* / Q000096:biosynthesis*; D012263:Ribonucleosides; D013056:Spectrophotometry, Ultraviolet; D013388:Succinimides; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D012263:Ribonucleosides; D013388:Succinimides; C015752:N-chlorosuccinimide; C000323:bromotubercidin; C028650:5-chlorotubercidin; D012313:RNA; D001974:Bromosuccinimide; D014372:Tubercidin