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Volume 80, Issue 8 (Jan 2008)

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

Barbara Nawrot
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
/ Beata Rębowska
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
/ Olga Michalak
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
/ Marek Bulkowski
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
/ Damian Błaziak
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
/ Piotr Guga
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
/ Wojciech J. Stec
  • Corresponding author
  • Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200880081859

Among the various classes of modified nucleotides and oligonucleotides, phosphorothioate analogs, in which the sugar-phosphate backbone is modified by the substitution of a sulfur atom for one of the nonbridging oxygen atoms, have been most extensively studied in both in vitro and in vivo experiments. However, this substitution induces P-chirality of the dinucleoside phosphorothioate moiety. Consequently, even short phosphorothioate oligonucleotides synthesized using standard chemical methods exist as mixtures of many diastereoisomers. In our laboratory, the oxathiaphospholane (OTP) method has been developed for a stereocontrolled synthesis of oligo(deoxyribonucleoside phosphorothioate)s. Recently, this approach has been extended to ribonucleoside derivatives, and stereodefined phosphorothioate diribonucleotides were incorporated into oligomers suitable for mechanistic studies on deoxyribozymes. Next, it was found that the OTP ring can be opened with nucleophiles as weak as the phosphate or pyrophosphate anion, giving rise to nucleoside α-thiopolyphosphates. Surprisingly, the reaction between nucleoside OTP and O,O-dialkyl H-phosphonate or O,O-dialkyl H-phosphonothioate led to nucleoside 5'-O-(α-thio-β-O,O-dialkyl-hypophosphate) or 5'-O-(α,β-dithio-β-O,O-dialkyl-hypophosphate), respectively, i.e., derivatives containing a direct P-P bond.

Keywords: deoxyribozyme; hypophosphates; nucleoside polyphosphates; PS-DNA; PS-RNA

Conference

CHEM-BIO-TECH-2007, a joint meeting of the IUPAC 1st Symposium on Chemical Biotechnology (ISCB-1) and the 8th Symposium on Bioorganic Chemistry (ISBOC-8), International Symposium on Bioorganic Chemistry, ISBOC, Bioorganic Chemistry, Turin, Italy, 2007-08-08–2007-08-11

References

  • 1.

    , P. C. Zamecnik, M. L. Stephenson. Proc. Natl. Acad. Sci. USA 75, 280 (1978).CrossrefGoogle Scholar

  • 2.

    S. T. Crooke. Therapeutic Applications of Oligonucleotides, Springer Verlag, Heidelberg (1995).Google Scholar

  • 3.

    C. A. Stein, A. M. Kreig (Eds.). Applied Antisense Oligonucleotide Technology, John Wiley, NewYork (1998).Google Scholar

  • 4.

    S. T. Crooke (Ed.). Handbook of Experimental Pharmacology: Antisense Research and Applications, 131, Springer Verlag, Berlin (1998).Google Scholar

  • 5.

    V. N. Soyfer, V. N. Potaman. Triple-Helical Nucleic Acids, Springer Verlag, New York (1996).Google Scholar

  • 6.

    , N. T. Thuong, C. Helene. Angew. Chem., Int. Ed. Engl. 32, 666 (1993).CrossrefGoogle Scholar

  • 7.

    C. Giovannangeli, C. Helene. Antisense Nucleic Acid Drug Dev. 7, 413 (1997).Google Scholar

  • 8.

    , J. Rossi. J. Chem. Biol. 6, 33 (1999).CrossrefGoogle Scholar

  • 9.

    , A. Michienzi, J. J. Rossi. Methods Enzymol. 341, 581 (2001).CrossrefGoogle Scholar

  • 10.

    , R. R. Breaker. Science 290, 2095 (2000).CrossrefGoogle Scholar

  • 11.

    , A. Fire, S. Xu, M. K. Montgomery, S. A. Kostas, S. E. Driver, C. C. Mello. Nature 391, 806 (1998).CrossrefGoogle Scholar

  • 12.

    , J. Biggs, E. Hersperger, P. S. Steeg, L. A. Liotta, A. Shearn. Cell 63, 933 (1990).CrossrefGoogle Scholar

  • 13.

    A. A. Bominaar, A. C. Molijin, M. Pestel, M. Veron, H. P. J. Van. EMBO J. 12, 2275 (1993).Google Scholar

  • 14.

    , P. S. Steeg, G. Bevilacqua, L. Kopper, U. P. Thorgeirsson, J. E. Talmadge, L. A. Liotta, M. E. Sobel. J. Natl. Cancer Inst. 80, 200 (1988).CrossrefGoogle Scholar

  • 15.

    , J. Herrick, B. Sclavi. Mol. Microbiol. 63, 22 (2007).CrossrefGoogle Scholar

  • 16.

    , C. H. V. Hoyle, R. H. Hilderman, J. J. Pintor, H. Schluter, B. F. King. Drug Develop. Res. 52, 260 (2001).CrossrefGoogle Scholar

  • 17.

    J. Luthje, J. Baringer, A. Ogilvie. Thromb. Haemost. 54, 469 (1985).Google Scholar

  • 18.

    , J. Luthje, A. Ogilvie. Biochem. Biophys. Res. Commun. 115, 253 (1983).CrossrefGoogle Scholar

  • 19.

    H. Flodgaard, H. Klenow. Biochem. J. 208, 737 (1982).Google Scholar

  • 20.

    , H. Schluter, E. Offers, G. Bruggemann, M. van der Giet, M. Tepel, E. Nordhoff, M. Karas, C. Spieker, H. Witzel, W. Zidek. Nature 367, 186 (1994).CrossrefGoogle Scholar

  • 21.

    , J. Jankowski, M. Tepel, M. van der Giet, I. M. Tente, L. Henning, R. Junker, W. Zidek, H. Schluter. J. Biol. Chem. 274, 23926 (1999).CrossrefGoogle Scholar

  • 22.

    J. Micklefield. Curr. Med. Chem. 8, 1157 (2001).CrossrefGoogle Scholar

  • 23.

    , R. Corradini, S. Sforza, T. Tedeschi, R. Marchelli. Chirality 19, 269 (2007).CrossrefGoogle Scholar

  • 24.

    F. Eckstein. Antisense Nucleic Acid Drug Develop. 10, 117 (2000).Google Scholar

  • 25.

    , L. Wang, S. Chen, T. Xu, K. Taghizadeh, J. S. Wishnok, X. Zhou, D. You, Z. Deng, P. C. Dedon. Nat. Chem. Biol. 3, 709 (2007).CrossrefGoogle Scholar

  • 26.

    , F. Eckstein. Angew. Chem., Int. Ed. Engl. 22, 423 (1983).CrossrefGoogle Scholar

  • 27.

    , F. Eckstein. Annu. Rev. Biochem. 54, 367 (1985).CrossrefGoogle Scholar

  • 28.

    , P. Guga. Curr. Top. Med. Chem. 7, 695 (2007).CrossrefGoogle Scholar

  • 29.

    W. J. Stec, G. Zon. In Natural Products Chemistry, R. I. Zalewski, J. J. Skolik (Eds.), pp. 495-509, Elsevier, Amsterdam (1985).Google Scholar

  • 30.

    M. Koziolkiewicz, B. Uznanski, W. J. Stec, G. Zon. Chem. Scr. 26, 251 (1986).Google Scholar

  • 31.

    , A. Murakami, Y. Tamura, H. Wada, K. Makino. Anal. Biochem. 233, 285 (1994).CrossrefGoogle Scholar

  • 32.

    , Y. Tamura, L. H. Miyoshi, T. Yokota, K. Makino. Nucleosides Nucleotides 17, 269 (1998).CrossrefGoogle Scholar

  • 33.

    , W. J. Stec, A. Grajkowski, B. Karwowski, A. Kobylanska, M. Koziolkiewicz, K. Misiura, A. Okruszek, A. Wilk, P. Guga, M. Boczkowska. J. Am. Chem. Soc. 117, 12019 (1995).CrossrefGoogle Scholar

  • 34.

    , W. J. Stec, B. Karwowski, M. Boczkowska, P. Guga, M. Koziolkiewicz, M. Sochacki, M. Wieczorek, J. Blaszczyk. J. Am. Chem. Soc. 120, 7156 (1998).CrossrefGoogle Scholar

  • 35.

    P. Guga, W. J. Stec. In Current Protocols in Nucleic Acid Chemistry, S. L. Beaucage, D. E. Bergstrom, G. D. Glick, R. A. Jones (Eds.), pp. 4.17.1-4.17.28, John Wiley, Hoboken, NJ (2003).Google Scholar

  • 36.

    W. J. Stec, Cz. S. Cierniewski, A. Okruszek, A. Kobylanska, Z. Pawlowska, M. Koziolkiewicz, E. Pluskota, A. Maciaszek, B. Rebowska, M. Stasiak. Antisense Nucleic Acids Drugs Dev. 7, 567 (1997).Google Scholar

  • 37.

    , T. Inagawa, H. Nakashima, B. Karwowski, P. Guga, W. J. Stec, H. Takeuchi, H. Takaku. FEBS Lett. 528, 48 (2002).CrossrefGoogle Scholar

  • 38.

    , M. Koziolkiewicz, A. Owczarek, K. Domanski, M. Nowak, P. Guga, W. J. Stec. Bioorg. Med. Chem. 9, 2403 (2001).CrossrefGoogle Scholar

  • 39.

    , M. Koziolkiewicz, A. Owczarek, M. Wojcik, K. Domanski, P. Guga, W. J. Stec. J. Am. Chem. Soc. 124, 4623 (2002).CrossrefGoogle Scholar

  • 40.

    , M. Boczkowska, P. Guga, B. Karwowski, A. Maciaszek. Biochemistry 39, 11057 (2000).CrossrefGoogle Scholar

  • 41.

    , B. Nawrot, K. Widera, M. Wojcik, B. Rebowska, G. Nowak, W. J. Stec. FEBS J. 274. 1062 (2007).CrossrefGoogle Scholar

  • 42.

    , P. A. Frey, R. D. Sammons. Science 228, 541 (1985).CrossrefGoogle Scholar

  • 43.

    , P. Guga, M. Boczkowska, M. Janicka, A. Maciaszek, S. Kuberski, W. J. Stec. Biophys. J. 92, 2507 (2007).CrossrefGoogle Scholar

  • 44.

    , P. Guga, M. Janicka, A. Maciaszek, B. Rebowska, G. Nowak. Biophys. J. 93, 3567 (2007).CrossrefGoogle Scholar

  • 45.

    , J. Wengel. Acc. Chem. Res. 32, 301 (1999).CrossrefGoogle Scholar

  • 46.

    , B. Karwowski, A. Okruszek, J. Wengel, W. J. Stec. Bioorg. Med. Chem. Lett. 11, 1001 (2001).CrossrefGoogle Scholar

  • 47.

    A. Krakowiak, R. Kaczmarek, J. Baraniak, M. Wieczorek, W. J. Stec. J. Chem. Soc. Chem. Commun. 2163 (2007).CrossrefGoogle Scholar

  • 48.

    R. Knoll, R. Bald, J. P. Furste. RNA 3, 132 (1997).Google Scholar

  • 49.

    , B. Nawrot, B. Rebowska, K. Cieslinska, W. J. Stec. Tetrahedron Lett. 46, 6641 (2005).CrossrefGoogle Scholar

  • 50.

    , N. Ota, M. Warashina, K. Hirano, K. Hatanaka, K. Taira. Nucleic Acids Res. 26, 3385 (1998).CrossrefGoogle Scholar

  • 51.

    P. M. J. Burgers, F. Eckstein, D. H. Hunneman. J. Biol. Chem. 254, 7476 (1979).Google Scholar

  • 52.

    , B. V. L. Potter, B. A. Connolly, F. Eckstein. Biochemistry 22, 1369 (1983).CrossrefGoogle Scholar

  • 53.

    , S. Pitsch, P. A. Weiss, L. Jenny, A. Stutz, X. Wu. Helv. Chim. Acta 84, 3773 (2001).CrossrefGoogle Scholar

  • 54.

    K. Misiura, K. Domanski, D. Korczynski. Unpublished results.Google Scholar

  • 55.

    K. Misiura. Unpublished results.Google Scholar

  • 56.

    , K. Misiura, D. Szymanowicz, W. J. Stec. Chem. Commun. 515 (1998).CrossrefGoogle Scholar

  • 57.

    , K. Misiura, D. Szymanowicz, W. J. Stec. Org. Lett. 7, 2217 (2005).CrossrefGoogle Scholar

  • 58.

    Tomaszewska, P. Guga, W. J. Stec. Unpublished results.Google Scholar

  • 59.

    J. Setondji, P. Remy, G. Dirheimer, J. P. Ebel. Biochim. Biophys. Acta 224, 136 (1970).Google Scholar

  • 60.

    J. Setondji, P. Remy, G. Dirheimer, J. P. Ebel. Biochim. Biophys. Acta 232, 585 (1971).Google Scholar

About the article

Published Online: 2009-01-01

Published in Print: 2008-01-01


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200880081859.

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