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1993 | 40 | 4 |
Tytuł artykułu

Z-RNA. The synthesis of 2'-O-[13C]methyl- and 5-methyl-analogs of ribo-CGCGCG

Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Chemical synthesis of 2'-0-[13C methyl-rCGCGCG and 5-methyl-rCGCGCG using support-aided phosphoramidite method is presented. 2'-0-Methyl guanosine derivative was separated from its 3'-0-methyl counterpart using transient 5',3'-0-silylation with l,3-dichloro-l,l,3,3-tetraisopropyldisiloxane (Markiewicz reagent). The hexamers were obtained in a purity suitable for NMR studies.
Wydawca
-
Rocznik
Tom
40
Numer
4
Opis fizyczny
p.521-530,fig.
Twórcy
autor
  • Polish Academy of Sciences, Z. Noskowskiego 12-14, 61-704 Poznan, Poland
autor
autor
autor
Bibliografia
  • 1. Hall, K., Cruz, P., Tmoco, I. Jr., Jovin, T.M. & Van de Sande, J.H. (1984) Z RNA. Left handed structure of poly[r(CG)]. Nature (London) 311, 584 - 589.
  • 2. Adamiak, R.W., Galat, A. & Skalski, B. (1985) Salt- and solvent-dependent conformational transitions of ribo-CGCGCG duplex. Biochim. Biophys. Acta 825,345 - 352.
  • 3. Davis, P.W., Adamiak, R.W. & Tmoco, I. Jr. (1990) Z-RNA; The solution NMR structure of r(CGCGCG). Biopolymers 29,109-122.
  • 4. Barone, A.D., Tang, J.-Y. & Caruthers, M.H. (1984) In situ activation of bisdialkylamino- phosphines - a new method for synthesizing deoxyoligonucleotides on solid support Nucleic Acids Res. 12,4051 - 4061.
  • 5. Markiewicz, W.T. (1979) Tetraisopropyldi- siloxane-l,3-diyl, a group for simultaneous protection of 3' and 5' hydroxy function of nucleosides. J. Chem. Res. (S) 24 - 25.
  • 6. Sung, W.L. & Narang, S.A. (1981) Synthesis of riboundecaadenylate and two fragments constituting the sequence of R-17 translation control signal. Can. J. Chem. 60, 111 -120.
  • 7. Inoue, H., Hayase, Y., Imura, A., Iwai, S. & Ohtsuka, E. (1987) Synthesis and hybridisation studies on two complementary nona(2'-0- -methyl)ribonucleotides. Nucleic Acids Res. 15, 6131 - 6148.
  • 8. Heikkila, J., Bjoerkman, S., Oeberg, B. & Chattopadhyaya, J. (1982) 5'-0-Trityl group promoted directive effect in the preparation of 2'-0-methylribonucleosides. Acta Chem. Scand. B 36,715 - 717.
  • 9. Milecki, J., Popenda, M. & Adamiak, R.W. (1993) NMR analysis of isomeric 2'(3')-0- -trialkylsilyl and 2'(3')-0-methyl ribonucleo­tides. Pol. J. Chem. in press.
  • 10. Fox, J.J., VanPraag, D., Wempen, I., Doerr, I.L., Cheong, L., Knoll, J.E., Eidinoff, M.L., Bendich, A. &Brown,G.B. (1953) Thiation of nucleosides. II. Synthesis of 5-methyl-2'-deoxycytidine and related pyrimidine nucleosides. J. Am. Chem. Soc. 81,178 - 187.
  • 11. Gait, M.J. (ed.) (1984) Oligonucleotide synthesis; a practical approach. IRL Press, Oxford, England.
  • 12. Beaucage, S.L. & Iyer, R.P. (1992) Advances in the synthesis of oligonucleotides by the phos- phoramidite approach. Tetrahedron 48, 2223 - 2311.
  • 13. Wagner, E., Oberhauser, B., Holzner, A., Brunar, H., Issakides, G., Schaffner, G., Cotten, M., Knollmueller, M. & Noe, Ch.R. (1991) A simple procedure for the preparation of protected 2'-0-methyI or 2'-0-ethyl ribonucleoside-3'- -O-phosphoramidites. Nucleic Acids Res. 19, 5965 - 5971
  • 14. Sproat, B.S., Beijer, B. & Iribarren, A. (1990) New synthetic routes to protected purine 2'-0-met- hylribonucleoside 3'-0-phosphoramidites using a novel alkylation procedure. Nucleic Acids Res. 18,41-49.
  • 15. Niedballa, U. & Vorbrueggen, H. (1974) A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides. }. Org. Chem. 39, 3654 - 3659.
  • 16. Sung, W.L. (1982) Synthesis of 4-(l,2,4-triazol- -l-yl)pyrimidin-2(lH)-one ribonucleotide and its application in synthesis of oligonucleotides. ]. Org. Chem. 47,3623 - 3628.
  • 17. McLaughlin, L.W., Piel, N. & Hellman, T. (1985) Preparation of protected ribonucleosides suitable for chemical oligoribonucleotide synthesis. Synthesis 322 - 323.
  • 18. Schmidt, S., Pein, C.-D., Fritz, H.-J. & Cech, D. (1992) Chemical synthesis of 2'-deoxyoligo- nucleotides containing 5-fIuoro-2'-deoxy- cytidine. Nucleic Acids Res. 20,2421 - 2426.
  • 19. Milecki, J., Dembek, P., Antkowiak, W.Z., Gdaniec, Z., Mielewczyk, S. & Adamiak, R.W. (1989) Application of 2'-0-tBDMSi group in chemical RNA synthesis. Part 1.31P NMR Study of 2'-0-tBDMSi group migration during 3'-OH phosphorylation and phosphitylation reactions. Nucleosides & Nucleotides 8, 463 - 474.
  • 20. Stawiński, J., Stroemberg, R., Thelin, M. & Westman, E. (1988) Studies on the t-butyl- dimethylsilyl group as 2'-0-protection in oligoribonucleotide synthesis via H-phospho- nate approach. Nucleic Acids Res. 16,9285 - 9298.
  • 21. Usman, N., Ogilvie, K.K., Jiang, M.-Y. & Cedergren, R.J. (1987) Automated chemical synthesis of long oligoribonucleotides using 2'-0-silylated ribonucleoside 3'-0-phospho- ramidites on a controlled pore glass support: Synthesis of a 43-nucleotide sequence similar to the 3'-half molecule of an E. coli formyl- methionine tRNA.). Am. Chem. Soc. 109,7845 - 7854.
  • 22. Ogilvie, K.K., Usman, N., Nicoghosian, K. & Cedergren, R.J. (1988) Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity. Proc. Natl. Acad. Sci. U.S.A. 85,5764 - 5768.
  • 23. Arnold, L., Smrt, J., Zajicek, J., Ott, G., Scheisswohl, M. & Sprinzl, M. (1991) Dimethylaminomethylene protected purine H-phosphonates in the synthesis of biologically active RNA (24-mer). Collect. Czech. Chem. Commun. 56,1948 -1956.
  • 24. Świderski, P.M., Bertrand, E. & Kaplan, B.E. (1993) Reverse phase ion-pair chromatography of oligonucleotides. Anal. Biochem. in press.
Typ dokumentu
Bibliografia
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Identyfikator YADDA
bwmeta1.element.agro-article-8bb6c696-7838-4081-a816-d8d1d714e061
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