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. 1975 Aug;2(8):1345-63.
doi: 10.1093/nar/2.8.1345.

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

M Ikehara, T Nagura, E Otsuka
Free PMC article

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

M Ikehara et al. Nucleic Acids Res. 1975 Aug.
Free PMC article

Abstract

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 W were synthesized. 3'-Phosphates of I, II and V were synthesized by phosphorylation using cyanoethylphosphate and DCC. In the case of II, 2', 3'-cyclic phosphate was directly obtained. 3'-Phosphates, thus obtained, were properly protected on 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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