1440. 5-Bromouracil
Nomenclature
CAS number: 51-20-7
5-Bromo-2,4(1H,3H)-pyrimidinedione. C4H3BrN2O2; mol wt 190.98.
C 25.16%, H 1.58%, Br 41.84%, N 14.67%, O 16.76%.
Description and references
Major chemical mutagen; incorporates into DNA, altering base-pair sequencing by replacing thymine. Prepn: H. L. Wheeler, H. F. Merriam, Am. Chem. J. 29, 478 (1903); P. A. Levene, F. B. LaForge, Ber. 45, 608 (1912). UV effects on DNA containing 5-bromouracil: A. G. Skavronskaya et al., Mutat. Res. 6, 319 (1968); F. Hutchinson, Q. Rev. Biophys. 6, 201 (1973). Mechanisms of mutagenesis: I. Pietrzykowska, Mutat. Res. 19, 1 (1973); E. M. Witkin, E. C. Parisi, ibid. 25, 407 (1974); B. Rydberg, Mol. Gen. Genet. 152, 19 (1977). Crystal structure and base stacking properties: H. Sternglanz, C. E. Bugg, Biochim. Biophys. Acta 378, 1 (1975).
