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. 1972 Jul;69(7):1855-7.
doi: 10.1073/pnas.69.7.1855.

5-Fluoro-2'-deoxyuridylate: covalent complex with thymidylate synthetase

D V Santi, C S McHenry

5-Fluoro-2'-deoxyuridylate: covalent complex with thymidylate synthetase

D V Santi et al. Proc Natl Acad Sci U S A. 1972 Jul.

Abstract

5-Fluoro-2'-deoxyuridylate causes a rapid inactivation of thymidylate synthetase that is dependent upon prior complexation of the cofactor 5,10-methylenetetrahydrofolate. The enzyme-5-fluoro-2'-deoxyuridylate complex may be isolated on nitrocellulose membranes and is not disrupted by 6 M urea. Upon reaction of 5-fluoro-2'-deoxyuridylate with the enzyme in the presence of 5,10-methylenetetrahydrofolate a rapid loss of absorbance is observed at 269 nm, the absorption maximum for the pyrimidine chromophore. It is concluded that a covalent bond is formed between the 6-position of 5-fluoro-2'-deoxyuridylate and a nucleophilic group of the enzyme that is involved in catalysis.

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