97511-53-0Relevant 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.
The First Example of a Mimic of the Overall Thymidylate Synthase Reaction
Meij, Paul F. C. van der,Chen, Tjoe B. R. A.,Hilhorst, Ellen,Waard, Eduard R. de,Pandit, Upendra K.
, p. 720 - 721 (2007/10/02)
2-Tosyl-1,2,3,13b-tetrahydroimidazophenanthridine functions as a mimic of the cofactor 5,10-methylenetetrahydrofolate in transferring both a methylene moiety and a hydride equivalent (i.e. an overall methyl group) to the C-5 position of a uracil derivative.
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
A Chemical Model of Thymidylate Synthetase. Formation of a Thymine Derivative via an Exocyclic Methylene Intermediate
Meij, Paul F. C. van der,Lohmann, Ruth D.,Waard, Eduard R. de,Chen, Tjoe B. R. A.,Pandit, Upendra K.
, p. 1229 - 1230 (2007/10/02)
Reaction of 6-aminouracil derivatives with imidazolidines (methylenetetrahydrofolate models), in the presence of acid, gives an exocyclic methylene intermediate which reacts with nucleophiles present in the mixture or can be reduced to a thymine derivative.
