The synthesis of carboxymethyl derivatives of purines and pyrimidines and their condensation with naturally occurring macromolecules

doi:10.1016/S0040-4020(01)93352-6

Tetrahedron

Volume 29, Issue 15, 1973, Pages 2293-2296

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Abstract

1-Carboxymethylthymine, 1-carboxymethylcytosine and 9-carboxymethyladenine were obtained by the direct carboxymethylation of the appropriate bases. In addition a small amount of 3-carboxymethyladenine was obtained. 9-Carboxymethylhypoxanthine was obtained by deamination of 9-carboxymethyladenine. 1-Carboxymethyluracil, 1-carboxymethylthymine and 9-carboxymethyl-hypoxanthine were each condensed with protamine and with dextran to give water-soluble, base-substituted polymers. The 1-carboxymethylthymine-dextran showed a slow decrease in optical density at 268 nm in 2 × SSC at 20°, of 30%. This did not occur in 7M urea. 1-Carboxymethylthymine-dextran gave an additional hypochromic effect with polyadenylic acid in 2 × SSC at 4° or 14° of 13% and 9% respectively. The ratio of thymine: adenine residues at the point of maximum hypochromicity was 3:1. The other dextran derivatives did not show similar hypochromic effects. The 1-carboxy-methylthymine-protamine gave a precipitate with polyadenylic acid probably due to electrostatic interaction.

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The synthesis of carboxymethyl derivatives of purines and pyrimidines and their condensation with naturally occurring macromolecules

Abstract

Biochim. et Biophys. Acta

Carbohydrate Research

Tetrahedron

Proc. Nat. Acad. Sci. U.S.

Proc. Nat. Acad. Sci. U.S.

Proc. Nat. Acad. Sci. U.S.

Proc. Nat. Acad. Sci. U.S.