Introduction of antigenic determining 2,4-dinitrophenyl residues into 4-thiouridine, N3-(3-L-amino-3-carboxypropyl) uridine and tRNAPhefrom E.coli

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Abstract
The introduction of antigenic determining 2,4-dinitrophenyl residues into the rare ribonucleosides 4-thiouridine (la), and N3-(3-L-amino-3-carboxy-propyUuridlne (2) as well as into tRNAPhe from E.coli has been investigated. Alkylation of 1a with ω-bromo-2,4-dinitroacetophenone (3b) gives S-(2,4-di-nitrophenacyl)-4-thiouridine (5a) . Applying the reaction to the 5′-monophos-phate 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-dlnitrobenzamido)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 tRNAPne from E.coli. The modified tENAPhe was isolated and by degradation of the molecule with RNaae T2 and alkaline phosphatase the nucleoside derivative 6 was obtained and found to be identical with the synthetic product.