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.
Full text
PDF


















Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Ikehara M., Kaneko M. Studies of nucleosides and nucleotides. XLI. Purine cyclonucleosides. 8. Selective sulfonylation of 8-bromoadenosine derivatives and an alternate synthesis of 8,2'-and 8,3'-S-cyclonucleosides. Tetrahedron. 1970 Sep;26(18):4251–4259. doi: 10.1016/s0040-4020(01)93068-6. [DOI] [PubMed] [Google Scholar]
- Ikehara M., Uesugi S. Studies on nucleosides and nucleotides. 38. Synthesis of 8-bromoadenosine nucleotides. Chem Pharm Bull (Tokyo) 1969 Feb;17(2):348–354. doi: 10.1248/cpb.17.348. [DOI] [PubMed] [Google Scholar]
- Ikehara M., Uesugi S., Yoshida K. Studies on the conformation of purine nucleosides and their 5'-phosphates. Biochemistry. 1972 Feb 29;11(5):830–836. doi: 10.1021/bi00755a023. [DOI] [PubMed] [Google Scholar]
- Lucas-Lenard J. Protein biosynthesis. Annu Rev Biochem. 1971;40:409–448. doi: 10.1146/annurev.bi.40.070171.002205. [DOI] [PubMed] [Google Scholar]
- NIRENBERG M., LEDER P. RNA CODEWORDS AND PROTEIN SYNTHESIS. THE EFFECT OF TRINUCLEOTIDES UPON THE BINDING OF SRNA TO RIBOSOMES. Science. 1964 Sep 25;145(3639):1399–1407. doi: 10.1126/science.145.3639.1399. [DOI] [PubMed] [Google Scholar]
- Prusiner P., Brennan T., Sundaralingam M. Crystal structure and molecular conformation of formycin monohydrates. Possible origin of the anomalous circular dichroic spectra in formycin mono- and polynucleotides. Biochemistry. 1973 Mar 13;12(6):1196–1202. doi: 10.1021/bi00730a028. [DOI] [PubMed] [Google Scholar]
- Sawa T., Fukagawa Y., Homma I., Takeuchi T., Umezawa H. Formycin-deaminating activity of microorganisms. J Antibiot (Tokyo) 1967 Nov;20(6):317–321. [PubMed] [Google Scholar]
- Tavale S. S., Sobell H. M. Crystal and molecular structure of 8-bromoguanosine and 8-bromoadenosine, two purine nucleosides in the syn conformation. J Mol Biol. 1970 Feb 28;48(1):109–123. doi: 10.1016/0022-2836(70)90222-6. [DOI] [PubMed] [Google Scholar]
