Introduction of antigenic determining 2,4-dinitrophenyl residues into 4-thiouridine, N3-(3-L-amino-3-carboxypropyl) uridine and tRNA-Phe from E. coli.
The introduction of antigenic determining 2,4-dinitrophenyl residues into the rare ribonucleosides 4-thiouridine (1a), and N3-(3-L-amino-3-carboxypropyl) uridine (2) as well as into tRNA-Phe from E. coli has been investigated. Alkylation of 1a with omega-bromo-2,4-dinitroacetophenone (3b) gives S-(2,4-dinitrophenacyl)-4-thiouridine (5A). Applying the reaction to the 5'-monophosphate of 1a, 5b is formed, but this product decomposes at pH 7. However, acylation of 2 with 2,4-dinitrobenzoic acid N-hydroxysuccinimide ester (4b) leads to N3-[3-carboxy-3-L-(2,4-dinitrobenzamido)propyl]uridine (6) which is stable in aqueous solution. The latter reaction was used for the introduction of an antigenic determining 2,4-dinitrophenyl residue into tRNA-Phe from E. coli. The modified tRNA-Phe was isolated and by degradation of the molecule with RNase T2 and alkaline phosphatase the nucleoside derivative 6 was obtained and found to be identical with the synthetic product.
D055598:Chemical Phenomena; D002621:Chemistry; D004136:Dinitrobenzenes; D000939:Epitopes; D004926:Escherichia coli; D006241:Haptens; D010649:Phenylalanine; D012343:RNA, Transfer / Q000276:immunology*; D013891:Thiouridine / Q000276:immunology*; D014529:Uridine / Q000031:analogs & derivatives* / Q000276:immunology
D004136:Dinitrobenzenes; D000939:Epitopes; D006241:Haptens; D013891:Thiouridine; D010649:Phenylalanine; D012343:RNA, Transfer; D014529:Uridine