13332-78-0Relevant academic research and scientific papers
MODELS OF FOLATE COFACTORS 17. METHYLATION OF 1,3-DIMETHYL-6-METHYLAMINO-URACIL BY A 5,10-CH2-H4FOLATE MODEL. THE FIRST MIMIC OF THE OVERALL dTMP SYNTHASE REACTION
Meij, Paul F.C. van der,Chen, Tjoe B.R.A.,Hilhorst, Ellen,Waard, Eduard R. De,Pandit, Upenda K.
, p. 4015 - 4022 (2007/10/02)
2-Tosyl-1,2,3,12b-tetrahydroimidazophenanthridine (6) was prepared in five steps from 6-chloromethylphenanthridine (1) in an overall yield of 50percent.The reaction of 6 with 1,3-dimethyl-6-methylaminouracil (8) in CH3CN/TFA (100:1) at 50-80 deg C, gave a mixture of products from which 1,3-dimethyl-6-methylaminothymine (9a) could be isolated.This constitutes a mimic of the overall dTMP synthase reaction in transferring both a methylene unit and a hydride equivalent from the cofactor model 6 to the 5-position of a uracil derivative.The other products which are formed in the reaction of 6 with 8 are derived from the reaction of the exocyclic intermediate C, formed in the carbon transfer step, with nucleophiles present in the reaction mixture.
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
