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Nucleic Acids Research, 1980, Vol. 8, No. 24 6213-6219
© 1980

CHEMISTRY

Halogenation of tubercidin by N-halosuccinimides. A direct route to 5-bromotubercidin, a reversible inhibitor of RNA synthesis in eukaryotic cells

Donald E. Bergstrom and Alan J. Brattesani

Department of Chemistry, University of North Dakota Grand Forks, ND 58202, USA

Received October 10, 1980. 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.


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