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Pure Appl. Chem., 2008, Vol. 80, No. 8, pp. 1859-1871

http://dx.doi.org/10.1351/pac200880081859

1,3,2-Oxathiaphospholane approach to the synthesis of P-chiral stereodefined analogs of oligonucleotides and biologically relevant nucleoside polyphosphates

Barbara Nawrot, Beata Rębowska, Olga Michalak, Marek Bulkowski, Damian Błaziak, Piotr Guga and Wojciech J. Stec

Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland

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  • Oka Natsuhisa, Murakami Ryosuke, Kondo Tomoaki, Wada Takeshi: Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag. Journal of Fluorine Chemistry 2013, 150, 85. <http://dx.doi.org/10.1016/j.jfluchem.2013.03.013>
  • Krsti�� Natalija M., Bjelakovi�� Mira S., Pavlovi�� Vladimir D., Robeyns Koen, Jurani�� Zorica D., Mati�� Ivana, Novakovi�� Irena, Sladi�� Du��an M., Iv��nyi Zolt��n, Szab�� Nikoletta, Huber Judit, W��lfling J��nos, Zupk�� Istv��n, Sz��csi Mih��ly, Wittmann Tibor, Schneider Gyula: New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. Steroids 2012, 77, 558. <http://dx.doi.org/10.1016/j.steroids.2012.01.021>
  • Nukaga Yohei, Yamada Kohei, Ogata Toshihiko, Oka Natsuhisa, Wada Takeshi: Stereocontrolled Solid-Phase Synthesis of Phosphorothioate Oligoribonucleotides Using 2′-O-(2-Cyanoethoxymethyl)-nucleoside 3′-O-Oxazaphospholidine Monomers. J. Org. Chem. 2012, 77, 7913. <http://dx.doi.org/10.1021/jo301052v>
  • Oka Natsuhisa, Wada Takeshi: Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms. Chemical Society Review 2011, 40, 5829. <http://dx.doi.org/10.1039/c1cs15102a>
  • Söderberg Linda, Lavén Gaston, Kalek Marcin, Stawinski Jacek: 31P NMR and Computational Studies on Stereochemistry of Conversion of Phosphoramidate Diesters into the Corresponding Phosphotriesters. NUCLEOT NUCL 2011, 30, 552. <http://dx.doi.org/10.1080/15257770.2011.586009>
  • Zon Gerald: Automated synthesis of phosphorus–sulfur analogs of nucleic acids—25 years on: potential therapeutic agents and proven utility in biotechnology. New J Chem 2010, 34, 795. <http://dx.doi.org/10.1039/b9nj00577c>
  • Wrzesinski Jan, Wichłacz Agnieszka, Nijakowska Danuta, Rebowska Beata, Nawrot Barbara, Ciesiołka Jerzy: Phosphate residues of antigenomic HDV ribozyme important for catalysis that are revealed by phosphorothioate modification. New J Chem 2010, 34, 1018. <http://dx.doi.org/10.1039/b9nj00727j>
  • Jemielity Jacek, Kowalska Joanna, Rydzik Anna Maria, Darzynkiewicz Edward: Synthetic mRNA cap analogs with a modified triphosphate bridge – synthesis, applications and prospects. New J Chem 2010, 34, 829. <http://dx.doi.org/10.1039/c0nj00041h>
  • Błaziak Damian, Guga Piotr, Jagiełło Agata, Korczyński Dariusz, Maciaszek Anna, Nowicka Anna, Pietkiewicz Aleksandra, Stec Wojciech J.: Stereoselective formation of a P–P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates. Org Biomol Chem 2010, 8, 5505. <http://dx.doi.org/10.1039/c0ob00104j>
  • Nawrot Barbara, Rebowska Beata, Michalak Olga, Bulkowski Marek, Blaziak Damian, Guga Piotr, Stec Wojciech J.: ChemInform Abstract: 1,3,2-Oxathiaphospholane Approach to the Synthesis of P-Chiral Stereodefined Analogues of Oligonucleotides and Biologically Relevant Nucleoside Polyphosphates. ChemInform 2009, 40. <http://dx.doi.org/10.1002/chin.200901253>
  • Dabkowski Wojciech, Kazimierczak Łucja: O-Methyl-bis-O-(4-nitrophenyl)phosphite: a novel chemoselective O-phosphitylating reagent. Tetrahetron Lett 2009, 50, 5035. <http://dx.doi.org/10.1016/j.tetlet.2009.06.102>