title: 5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.
abstract: The 5'-phosphate (1) of the antiviral nucleoside 5-cyano-2'-deoxyuridine was synthesized and evaluated for inhibition of thymidylate synthetase purified from methotrexate-resistant Lactobacillus casei. Compound 1 was a potent competitive inhibitor with a K1 of 0.55 microns. Irreversible enzyme inhibition by this compound could not be detected.
mesh_terms: D003856:Deoxyuracil Nucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D007780:Lacticaseibacillus casei / Q000201:enzymology; D008780:Methyltransferases / Q000037:antagonists & inhibitors*; D009570:Nitriles / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013940:Thymidylate Synthase / Q000037:antagonists & inhibitors*
chemical_list: C021165:5-cyano-2'-deoxyuridine 5'-phosphate; D003856:Deoxyuracil Nucleotides; D009570:Nitriles; D008780:Methyltransferases; D013940:Thymidylate Synthase