Studies on deoxyribonucleic acids and related compounds. III. Synthesis of oligodeoxyribonucleotides complementary to the anticodon loop of Escherichia coli tRNA by an improved triester method.

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Abstract
P-Chlorophenyl N-(p-methoxyphenyl)chlorophosphoramidate was used to phosphorylate the 3''-hydroxyl groups of N,5''-O-protected deoxyribonucleosides. These nucleotides served as the 3''-terminal unit in the synthesis of fully protected oligonucleotides, and the p-anisidine was readily removed by treatment with isoamyl nitrite to generate the 3''-phosphodiester for condensations. This approach was suitable for complete purification of fully protected oligonucleotides by chromatography, which was essential to obtain products. Deoxyoligonucleotides complementary to the anticodon loop of E. coli tRNA-f/met were synthesized by condensation of di-, tri- and tetranucleotide blocks (dATp, dTATp and dTTATp) with protected dGAG. The products (dATGAG, dTATGAG and dTTATGAG) were isolated by anion-exchange or reverse phase high pressure liquid chromatography.