5-Bromouracil, a highly mutagenic compound (that is, a compound that causes changes in DNA), is used in cancer chemotherapy. When administeredto a patient, it is converted to the triphosphate and incorporated into DNA in place of thymine, which it resembles sterically. Why does it causemutations?(Hint: The bromo substituent increases the stability of the enol tautomer.)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.SE: Something Extra
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5-Bromouracil, a highly mutagenic compound (that is, a compound that causes changes in DNA), is used in cancer chemotherapy. When administered
to a patient, it is converted to the triphosphate and incorporated into DNA in place of thymine, which it resembles sterically. Why does it cause
mutations?
(Hint: The bromo substituent increases the stability of the enol tautomer.)

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