Studies on transfer ribonucleic acids and related compounds. XXXVIII. A rapid method for the synthesis of ribooligonucleotides by using 3',5'-unsubstituted nucleosides. Synthesis of a hexanucleotide containing anticodon triplet of E. coli tRNAfMet.

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Abstract
N-Protected 2''-O-(o-nitrobenzyl)nucleosides were used as condensing units with protected nucleoside 3''-phosphates. After formation of the 3''-5'' linkage, the 3''-hydroxyl group of the dinucleoside monophosphate was phosphorylated by treatment with ether p-chlorophenyl phosphate plus DCC or p-chlorophenyl phosphoroditriazolide. The dinucleotide was further elongated in the 3''-direction by condensation with the N- and 2''-O-protected nucleosides followed by phosphorylation. Protected C-Gp and C-A-Up were prepared by this procedure. The trimer was used in the synthesis of hexamer C-A-U-A-A-C by condensation with the 3''-O-(o-nitrobenzyl)-containing trimer block. This hexamer corresponds to the bases 35 to 40 of E. coli formylmethionyl tRNA, which are located in the anticodon loop. A trimer containing uridine in the middle position was also synthesized by this method in combination with an extraction procedure for the intermediate to permit rapid isolation.