Studies on transfer ribonucleic acids and related compounds. X. Synthesis of the yeast tyrosine tRNA 5'-terminal oligonucleotides.

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The pentanucleotide which has the sequence of 8th to 12th base of the 5'-terminus of yeast tyrosine transfer ribonucleic acid (tRNA), UpApm2GpCpC (1) has been synthesized by stepwise addition of properly protected mononucleotides using dicyolohexylcarbodiimide. 5'-O-Monomethoxytrityl-N2-methylguanosine 3'-phosphate was prepared by phosphorylation of the 5'-protected nucleoside to give the 2', 3'-cyclic phosphate and successive hydrolysis with ribonuclease (RNase) St. The isolated yields of the protected ditri, tetra-, and penta-nucleotides were 75, 38, 31, and 21%, respectively. The 5'-terminal tetranucleotide CpUpCpUp (3) corresponding to 1st to 4th nucleotides, was synthesized by condensation of the dinucleotide, Bz-CBz (OBz)-pU (OBz)-p (14) and the anilidate, CBz (OBz)-pU-(OBz)-pNHPh (16b) in a yield of 22%. The trinucleotide CpGpGp (2) spanning 5th to 7th nucleotides from the 5'-end was also prepared by the amidate method from the dinucleotide, MMTrCBz (OBz)-pGBu (OiBu)-p(18) and G1Bu (OiBu)-pNHPhOCH3 (19b) in a yield of 17%.

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