Synthesis and triplex-forming properties of oligonucleotides containing thio-substituted C-nucleoside 4-thiopseudoisocytidine

作者: Shi-Qi Cao , Itaru Okamoto , Hirosuke Tsunoda , Akihiro Ohkubo , Kohji Seio

DOI: 10.1016/J.TETLET.2010.11.065

关键词: Thermal denaturationC nucleosidesDisulfide bondThermal stabilityStereochemistryThio-NucleosideChemistryOrganic chemistryOligonucleotide

摘要: Abstract We synthesized the 3′-phosphoramidite building block of 4-thiopseudoisocytidine (s 4 Ψ i C) and incorporated it into triplex-forming oligonucleotides (TFOs). The results thermal denaturation triplexes incorporating s C showed that could be used as a nucleoside component TFOs to increase stability at pH 7.

参考文章(22)
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
Itaru Okamoto, Shiqi Cao, Hiroto Tanaka, Kohji Seio, Mitsuo Sekine, Synthesis of 4-Thiopseudoisocytidine and 4-Thiopseudouridine as Components of Triplex-forming Oligonucleotides Chemistry Letters. ,vol. 38, pp. 174- 175 ,(2009) , 10.1246/CL.2009.174
Matthieu Sollogoub, Keith R. Fox, Vicki E.C. Powers, Tom Brown, First synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine Tetrahedron Letters. ,vol. 43, pp. 3121- 3123 ,(2002) , 10.1016/S0040-4039(02)00481-1
Frank B. Howard, Joe Frazier, Marie N. Lipsett, H.Todd Miles, Infrared demonstration of two- and three-strand helix formation between poly C and guanosine mononucleotides and oligonucleotides Biochemical and Biophysical Research Communications. ,vol. 17, pp. 93- 102 ,(1964) , 10.1016/0006-291X(64)90306-7
Taifeng Wu, Kelvin K. Ogilvie, Richard T. Pon, Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides. Nucleic Acids Research. ,vol. 17, pp. 3501- 3517 ,(1989) , 10.1093/NAR/17.9.3501
Itaru Okamoto, Kohji Seio, Mitsuo Sekine, Improved synthesis of oligonucleotides containing 2-thiouridine derivatives by use of diluted iodine solution Tetrahedron Letters. ,vol. 47, pp. 583- 585 ,(2006) , 10.1016/J.TETLET.2005.11.044
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
Stephen A. Scaringe, Christopher Francklyn, Nassim Usman, Chemical synthesis of biologically active oligoribonucleotides using beta-cyanoethyl protected ribonucleoside phosphoramidites. Nucleic Acids Research. ,vol. 18, pp. 5433- 5441 ,(1990) , 10.1093/NAR/18.18.5433
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