89367-55-5Relevant academic research and scientific papers
MODELS OF FOLATE COENZYMES 16. CHEMICAL MODELLING OF THE THYMIDYLATE SYNTHASE REACTION. EVIDENCE FOR AN "EXOCYCLIC METHYLENE INTERMEDIATE" ANALOGUE, WHICH IS REDUCIBLE TO A THYMINE DERIVATIVE, IN THE REACTION OF 6-AMINOURACILS WITH A 5,10-METHYLENETETRAHY
Meij, Paul F. C. van der,Lohmann, Ruth D.,Waard, Eduard R. De,Chen, Tjoe B. R. A.,Pandit, Upendra K.
, p. 3921 - 3930 (2007/10/02)
Reactions of 6-amino-, 6-alkylamino-, and 6-anilino-1,3-dimethyluracils (1a-1e) with 3,4-diphenyl-1-tosylimidazolidine (2), in the presence of acid, lead to the formation of products which are derived from an "exocyclic methylene intermediate" analogous t
MODELS OF FOLATE COENZYMES-VII SYNTHESIS AND CARBON TRANSFER REACTIONS OF N5,N10-METHENYL AND N5,N10-METHYLENETETRAHYDROFOLATE MODELS
Bieraeugel, H.,Plemp, R.,Hiemstra, H. C.,Pandit, U. K.
, p. 3971 - 3980 (2007/10/02)
Carboxylate esters react with 1,2-diaminoethanes to yield imidazolines, which upon consecutive reaction with acetic anhydride or tosyl chloride and methyl iodide give imidazolinium salts that serve as models of N5,N10-(CH+)-tetrahydrofolate (THF) coenzymes (7a,b and 18a,b).Reduction of the latter salts with sodium borohydride or reaction with anions (R-) give the corresponding 5,10--THF models.Mono- and bifunctional nucleophiles react with 18a,b to yield carbon-transfer products. 6-Alkylamino-1,3-dimethyluracils react with 1-tosyl-3,4,4-trimethylimidazolidine (the reduction product of 18b), in the presence of acetic acid, to form carbon-transfer products via a mechanism which bears close analogy to the mechanism of action of thymidylate synthetase.
