Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1989, 54, 523-532
https://doi.org/10.1135/cccc19890523

Automated chloridite and amidite synthesis of oligodeoxyribonucleotides on a long chain support using amidine protected purine nucleosides

Luboš Arnolda, Zdeněk Točíka, Eliška Bradkováa, Zdeněk Hostomskýb, Václav Pačesb and Jiří Smrta

a Institute of Organic Chemistry and Biochemistry
b Institute of Molecular Genetics, Czechoslovak Academy of Sciences, 166 10 Prague 6

Crossref Cited-by Linking

  • Cordes David B., Smiglak Marcin, Hines C. Corey, Bridges Nicholas J., Dilip Meghna, Srinivasan Geetha, Metlen Andreas, Rogers Robin D.: Ionic Liquid‐Based Routes to Conversion or Reuse of Recycled Ammonium Perchlorate. Chemistry A European J 2009, 15, 13441. <https://doi.org/10.1002/chem.200901217>
  • Mano Erina, Hyodo Mamoru, Sato Yumi, Ishihara Yuka, Ohta Michio, Hayakawa Yoshihiro: Synthesis of Cyclic Bis(3′‐5′)‐2′‐deoxyguanylic/guanylic Acid (c‐dGpGp) and Its Biological Activities to Microbes. ChemMedChem 2007, 2, 1410. <https://doi.org/10.1002/cmdc.200700072>
  • Nurminen Erkki, Lönnberg Harri: Mechanisms of the substitution reactions of phosphoramidites and their congeners. J of Physical Organic Chem 2004, 17, 1. <https://doi.org/10.1002/poc.681>
  • Hayakawa Yoshihiro, Kawai Rie, Hirata Akiyoshi, Sugimoto Jun-ichiro, Kataoka Masanori, Sakakura Akira, Hirose Masaaki, Noyori Ryoji: Acid/Azole Complexes as Highly Effective Promoters in the Synthesis of DNA and RNA Oligomers via the Phosphoramidite Method. J. Am. Chem. Soc. 2001, 123, 8165. <https://doi.org/10.1021/ja010078v>
  • Hayakawa Yoshihiro: Toward an Ideal Synthesis of Oligonucleotides: Development of a Novel Phosphoramidite Method with High Capability. Bulletin of the Chemical Society of Japan 2001, 74, 1547. <https://doi.org/10.1246/bcsj.74.1547>
  • Pon Richard T.: Solid‐Phase Supports for Oligonucleotide Synthesis. CP Nucleic Acid Chemistry 2000, 00. <https://doi.org/10.1002/0471142700.nc0301s00>
  • Beaucage Serge L., Caruthers Marvin H.: Synthetic Strategies and Parameters Involved in the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method. CP Nucleic Acid Chemistry 2000, 00. <https://doi.org/10.1002/0471142700.nc0303s00>
  • Moriguchi Tomohisa, Yanagi Terukazu, Kunimori Masao, Wada Takeshi, Sekine Mitsuo: Synthesis and Properties of Aminoacylamido-AMP:  Chemical Optimization for the Construction of an N-Acyl Phosphoramidate Linkage. J. Org. Chem. 2000, 65, 8229. <https://doi.org/10.1021/jo0008338>
  • Vincent Stéphane, Mioskowski Charles, Lebeau Luc: Hydrolysis and Hydrogenolysis of Formamidines:  N,N-Dimethyl and N,N-Dibenzyl Formamidines as Protective Groups for Primary Amines. J. Org. Chem. 1999, 64, 991. <https://doi.org/10.1021/jo980099g>
  • Kurz Markus, Göbel Karin, Hartel Christian, Göbel Michael W.: Acridine‐Labeled Primers as Tools for the Study of Nonenzymatic RNA Oligomerization. Helvetica Chimica Acta 1998, 81, 1156. <https://doi.org/10.1002/hlca.19980810528>
  • Zhang Xiaohu, Abad José-Luis, Huang Qingtao, Zeng Fan, Gaffney Barbara L., Jones Roger A.: High yield protection of purine ribonucleosides for H-phosphonate RNA synthesis. Tetrahetron Lett 1997, 38, 7135. <https://doi.org/10.1016/S0040-4039(97)01767-X>
  • Andrus Alex, Vinayak Ravi, Kuimelis Robert G., Mullah Bashar: Targeted Gene Correction: Synthesis and Characterization of Double-Hairpin 2′-O-Methyl RNA/DNA Chimera Oligonucleotides. Nucleosides and Nucleotides 1997, 16, 1183. <https://doi.org/10.1080/07328319708006155>
  • Kypr Jaroslav, Chládková Jana, Arnold Luboš, Sági János, Szemzö Attila, Vorlíčková Michaela: The Unusual X-Form DNA in Oligodeoxynucleotides: Dependence of Stability on the Base Sequence and Length. Journal of Biomolecular Structure & Dynamics 1996, 13, 999. <https://doi.org/10.1080/07391102.1996.10508914>
  • Kovanda Jiří, Kejnovský Eduard, Arnold Luboš, Kypr Jaroslav: UV Light-Induced Crosslinking of Short DNA Duplex Strands: Nucleotide Sequence Preferences and a Prominent Role of the Duplex Ends. Journal of Biomolecular Structure & Dynamics 1996, 14, 57. <https://doi.org/10.1080/07391102.1996.10508929>
  • Mullah Bashar, Andrus Alex, Zhao Hong, Jones Roger A.: Oxidative conversion of N-dimethylformamidine nucleosides to N-cyano nucleosides. Tetrahedron Letters 1995, 36, 4373. <https://doi.org/10.1016/0040-4039(95)00816-U>
  • Piunno Paul A. E., Krull Ulrich J., Hudson Robert H. E., Damha Masad J., Cohen Huguette.: Fiber-Optic DNA Sensor for Fluorometric Nucleic Acid Determination. Anal. Chem. 1995, 67, 2635. <https://doi.org/10.1021/ac00111a022>
  • Piunno Paul A.E., Krull Ulrich J., Hudson Robert H.E., Damha Masad J., Cohen Huguette: Fiber optic biosensor for fluorimetric detection of DNA hybridization. Analytica Chimica Acta 1994, 288, 205. <https://doi.org/10.1016/0003-2670(93)E0611-A>
  • Robles Jordi, Pedroso Enrique, Grandas Anna: Stepwise solid-phase synthesis of nucleopeptide Phac-Ser(p5′CATCAT)-Gly-Asp-OH from adenovirus-2 nucleoprotein. Tetrahetron Lett 1994, 35, 4449. <https://doi.org/10.1016/S0040-4039(00)73381-8>
  • Ott Gunther, Arnold Lubos, Smrt Jiri, Sobkowski Michal, Limmer Stefan, Hofmann Hans-Peter, Sprinzl Mathias: The Chemical Synthesis of Biochemically Active Oligoribonucleotides Using Dimethylaminomethylene Protected Purine H-Phosphonates. Nucleosides and Nucleotides 1994, 13, 1069. <https://doi.org/10.1080/15257779408011880>
  • Koizume Shiro, Kamiya Hiroyuki, Inoue Hideo, Ohtsuka Eiko: Synthesis and Thermodynamic Stabilities of Damaged DNA Involving 8-Hydroxyguanine (7,8-Dihydro-8-Oxoguanine) in a ras-Gene Fragments. Nucleosides and Nucleotides 1994, 13, 1517. <https://doi.org/10.1080/15257779408012168>
  • Rosenberg Ivan, Soler Jaume Farras, Tocik Zdenek, Ren Wu-Yon, Ciszewski Lech A., Kois Pavol, Pankiewicz Krzysztof W., Spassova Maria, Watanabe Kyoichi A.: Synthesis of Oligodeoxynucleotides Containing the C-Nucleoside and 2′- Deoxy-2′-Fluoro-ara-Nucleoside Moieties by the H-Phosphonate Method.1,2. Nucleosides and Nucleotides 1993, 12, 381. <https://doi.org/10.1080/07328319308017834>
  • Beaucage Serge L., Iyer Radhakrishman P.: Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach. Tetrahedron 1992, 48, 2223. <https://doi.org/10.1016/S0040-4020(01)88752-4>
  • Vu Huynh, McCollum Christie, Jacobson Karen, Theisen Pete, Vinayak Ravi, Spiess Elizabeth, Andrus Alex: Fast oligonucleotide deprotection phosphoramidite chemistry for DNA synthesis. Tetrahetron Lett 1990, 31, 7269. <https://doi.org/10.1016/S0040-4039(00)88541-X>