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Nucleic Acids Research, 1977, Vol. 4, No. 3 711-722
© 1977

Articles

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

Frank Seela+, Fritz Hansske+, Kimitsuna Watanabe* and Friedrich Cramer+

+Max-Planck-lnstrtut für Experimentelte Medizin Abt.Chemie, Hermann-Rein-Str. 3, D-3400 Göttingen *Universität Paderborn - Gesamthochschule, Lab.für Bioorganische Chemie Warburger Str. 100, D-4790 Paderborn, GFR

Received January 27, 1977. 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 {omega}-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.


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