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Nucleic Acids Research, 1975, Vol. 2, No. 8 1345-1364
© 1975

Articles

Polynucleotides. XXXI1. Synthesis of AUG analogs containing 8,2'-S-cycloadenoslne, 8,5'-S-cycloadenosine, 8-bromoadenosine, 8-oxyadenosine and formycin in the first position of the codon

Morio Ikehara, Takeo Nagura and Eiko Ohtsuka

Faculty of Pharmaceutical Sciences, Osaka University Suita, Osaka, Japan 565

Received June 18, 1975. Five AUG analogs having 8,2'-S-cycloadenosine (I), 8,5'-S-cycloadenosine (II), 8-bromoadenosine (III), 8-oxyadenosine (IV) and formycin (V) in the first position of ApUpG were synthesized. 3'-Phosphates of I, II and V were synthesized by phosphorylation using cyanoethylphosphate and DCC. In the case of II, 2',3'-cyclicphosphate was directly obtained. 3'-Phosphates, thus obtained, were properly protectedon the 2'-OH and/or the N6-amino group and condensed with U(OBz)pGiBu(iBu)2 using DCC to give ApUpG analogs. Some properties on paper chromatography and electrophoresis, and the UV and CD spectra of these trinucleoside diphosphates are reported.


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