Synthesis of 4-Thiopseudoisocytidine and 4-Thiopseudouridine as Components of Triplex-forming Oligonucleotides
作者： Itaru Okamoto , Shiqi Cao , Hiroto Tanaka , Kohji Seio , Mitsuo Sekine
DOI: 10.1246/CL.2009.174
关键词:
摘要: In this paper, we report convenient methods for the synthesis of 4-thiopseudoisocytidine (s 4 ψiC) and 4-thiopseudouridine Ψ), 1 HNMR spectral analysis these modified nucleosides showed that both s Ψ ψiC prefer C3'-endo ribose puckering. These conformational properties are favorable stabilization triplex formation.
csj.jp参考文章(25)
Itaru Okamoto, Kohji Seio, Mitsuo Sekine, Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine. Bioorganic & Medicinal Chemistry Letters. ,vol. 16, pp. 3334- 3336 ,(2006) , 10.1016/J.BMCL.2006.02.019
Hanna Sierzputowska-Gracz, Elzbieta Sochacka, Andrzej Malkiewicz, Kenneth Kuo, Charles W. Gehrke, Paul F. Agris, Chemistry and structure of modified uridines in the anticodon, wobble position of transfer RNA are determined by thiolation Journal of the American Chemical Society. ,vol. 109, pp. 7171- 7177 ,(1987) , 10.1021/JA00257A044
Robert S. Coleman, Edward A. Kesicki, Synthesis and Postsynthetic Modification of Oligodeoxynucleotides Containing 4-Thio-2'-deoxyuridine (ds4U) Journal of the American Chemical Society. ,vol. 116, pp. 11636- 11642 ,(1994) , 10.1021/JA00105A002
Ulrike von Krosigk, Steven A. Benner, pH-Independent Triple Helix Formation by an Oligonucleotide Containing a Pyrazine Donor-Donor-Acceptor Base Journal of the American Chemical Society. ,vol. 117, pp. 5361- 5362 ,(1995) , 10.1021/JA00124A020
Paul F. Agris, Hanna Sierzputowska-Gracz, Wanda Smith, A. Malkiewicz, Elzbieta Sochacka, Barbara Nawrot, Thiolation of uridine carbon-2 restricts the motional dynamics of the transfer RNA wobble position nucleoside Journal of the American Chemical Society. ,vol. 114, pp. 2652- 2656 ,(1992) , 10.1021/JA00033A044
Guobing Xiang, Walid Soussou, Larry W. McLaughlin, A New Pyrimidine Nucleoside (m5oxC) for the pH-Independent Recognition of G-C Base Pairs by Oligonucleotide-Directed Triplex Formation Journal of the American Chemical Society. ,vol. 116, pp. 11155- 11156 ,(1994) , 10.1021/JA00103A040
Akira Ono, Paul O. P. Ts'o, Lou Sing Kan, Triplex formation of an oligonucleotide containing 2'-O-methylpseudoisocytidine with a DNA duplex at neutral pH Journal of Organic Chemistry. ,vol. 57, pp. 3225- 3230 ,(1992) , 10.1021/JO00037A048
Ramareddy V Guntaka, Balwantkumar R Varma, Karl T Weber, Triplex-forming oligonucleotides as modulators of gene expression. The International Journal of Biochemistry & Cell Biology. ,vol. 35, pp. 22- 31 ,(2003) , 10.1016/S1357-2725(02)00165-6
Akira Ono, Paul O. P. Ts'o, Lou Sing Kan, Triplex formation of oligonucleotides containing 2'-O-methylpseudoisocytidine in substitution for 2'-deoxycytidine Journal of the American Chemical Society. ,vol. 113, pp. 4032- 4033 ,(1991) , 10.1021/JA00010A077
Rainer Berressem, Joachim W. Engels, 6-Oxocytidine a novel protonated C-base analogue for stable triple helix formation Nucleic Acids Research. ,vol. 23, pp. 3465- 3472 ,(1995) , 10.1093/NAR/23.17.3465