Chemical modelling of the thymidylate synthase reaction: evidence for the formation of an exocyclic methylene intermediate from analogues of the covalent ternary complex formed by intramolecular thiol addition to C(6) of 5-aminomethyluracil derivatives.

✍ Scribed by Paul F.C. van der Meij; Upendra K. Pandit

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 258 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82891-9

✦ Synopsis

The intramolecular thiol addition to C(6) in 1-(3-mercaptopropyl)-5-aminomethyluracil derivatives in protic media leads to the formation of bicyclic 5,6_dihydrouracil derivatives, which may be regarded as models of the covalent ternary complex in the thymidylate synthase reaction. Evidence is presented for the formation of an exocyclic methylene intermediate from these model compounds.