Advertisement

Russian Journal of Bioorganic Chemistry

, Volume 44, Issue 2, pp 252–255 | Cite as

New Synthetic Route to CY5-Labeled 2'-Deoxycytidine- 5'-Triphosphates Using Sonogashira Reaction

  • T. O. Guseinov
  • V. E. Kuznetsova
  • V. E. Shershov
  • M. A. Spitsyn
  • S. A. Lapa
  • A. S. Zasedatelev
  • A. V. Chudinov
Letters to the Editor
First Online:
Received:
Accepted:
  • 32 Downloads

Abstract

Herein, we present a new synthetic route to fluorescently-labeled nucleoside triphosphates via Sonogashira cross-coupling of iodinated deoxycytidine monophosphate and cyanine dye with a terminal alkyne group.

Keywords

alkynylated nucleoside monophosphates fluorescently labeled nucleotides indodicarbocyanine dyes Sonogashira reaction 

Abbreviations

PCR

polymerase chain reaction

DIPEA

N,Ndiisopropylethylamine

DTDP

4,4'-dithiodipyridine

HBTU

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

5-IdCMP

5-iodo-2'-deoxycytidine-5'-monophosphate sodium salt

Im

imidazole

TBAP

tributylammonium pyrophosphate

This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kore, A.R., Senthilvelan, A., Snanmugasundaram, M., Sandoval, D., and Pardo, A., Nucleosides Nucleotides Nucleic Acids, 2015, vol. 34, pp. 221–228.CrossRefPubMedGoogle Scholar
  2. 2.
    Kore, A.R. and Charles, I., Current Org. Chem., 2012, vol. 16, pp. 1996–2013.CrossRefGoogle Scholar
  3. 3.
    Ramsay, N., Jemth, A., Brown, A., Crampton, N., Dear, P., and Holliger, Ph., J. Am. Chem. Soc., 2010, vol. 132, pp. 5096–5104.CrossRefPubMedPubMedCentralGoogle Scholar
  4. 4.
    Giller, G., Tasara, T., Angerer, B., Muhlegger, K., Amacker, M., and Winter, H., Nucleic Acids Res., 2003, vol. 31, pp. 2630–2635.CrossRefPubMedPubMedCentralGoogle Scholar
  5. 5.
    Brazier, J.A., Shibata, T., Townsley, J., Taylor, B.F., Frary, E., Williams, N.H., and Williams, D.M., Nucleic Acids Res., 2005, vol. 33, pp. 1362–1371.CrossRefPubMedPubMedCentralGoogle Scholar
  6. 6.
    Kuwahara, M., Nagashima, J., Hasegawa, M., Tamura, T., Kitagata, R., Hanawa, K., Hososhima, S., Kasamatsu, T., Ozaki, H., and Sawai, H., Nucleic Acids Res., 2006, vol. 34, pp. 5383–5394.CrossRefPubMedPubMedCentralGoogle Scholar
  7. 7.
    Henegariu, O., Bray-Ward, P., and Ward, D.C., Nat. Biotechnol., 2000, vol. 18, pp. 345–348.CrossRefPubMedGoogle Scholar
  8. 8.
    Anderson, J.P., Angerer, B., and Loeb, L.A., BioTechniques, 2005, vol. 38, no. 2, pp. 257–264.CrossRefPubMedGoogle Scholar
  9. 9.
    Herve, G. and Len, Ch., Sustain. Chem. Proc., 2015, no. 3, p. 3.CrossRefGoogle Scholar
  10. 10.
    Korshun, V.A., Manasova, E.V., and Berlin, Yu.A., Bioorg Khim., 1997, vol. 23, no. 5, pp. 324–387.Google Scholar
  11. 11.
    Prober, J.M., Trainor, G.L., Dam, R.J., Hobbs, F.W., Robertson, Ch.W., Zagusky, R.J., Cocuzza, A.J., Jensen, M.A., and Baumeister, K., Science, 1987, vol. 238, pp. 336–341.CrossRefPubMedGoogle Scholar
  12. 12.
    Confalone, Pat.N., J. Heterocycl. Chem., 1990, vol. 27, pp. 31–46.CrossRefGoogle Scholar
  13. 13.
    Seo, Y.J., Malyshev, D.A., Lavergne, Th., Ordoukhanian, Ph., and Romesberg, F.E., J. Am Chem. Soc., 2011, vol. 133, no. 49, pp. 19878–19888.CrossRefPubMedPubMedCentralGoogle Scholar
  14. 14.
    Dziuba, D., Pohla, R., and Hocek, M., Chem. Comm., 2015, vol. 51, pp. 4880–4882.CrossRefPubMedGoogle Scholar
  15. 15.
    Kielkowski, P., Cahova, H., Pohl, R., and Hocek, M., Bioorg. Med. Chem., 2016, vol. 24, pp. 1268–1276.CrossRefPubMedGoogle Scholar
  16. 16.
    Hocek, M., Org. Chem., 2014, vol. 79, pp. 9914–9921.CrossRefGoogle Scholar
  17. 17.
    Fegan, A., Shirude, P.S., and Balasubramanian, S., Chem. Commun., 2008, pp. 2004–2006.Google Scholar
  18. 18.
    Kuznetsova, V.E., Spitsyn, M.A., Shershov, V.E., Guseinov, T.O., Fesenko, E.E., Lapa, S.A., Ikonnikova, A.Yu., Avdonina, M.A., Nasedkina, T.V., Zasedatelev, A.S., and Chudinov, A.V., Mend. Commun., 2016, vol. 26, pp. 95–98.CrossRefGoogle Scholar
  19. 19.
    Hutter, D., Kim, M.J., Karalkar, N., Leal, N.A., Chen, F., Guggenheim, E., Visalakshi, V., Olejnik, J., Gordon, S., and Benner, S.A., Nucleosides Nucleotides Nucleic Acids, 2010, vol. 29, no. 11, pp. 879–895.CrossRefPubMedGoogle Scholar
  20. 20.
    Dourtoglou, V. and Gross, B., Synthesis, 1984, vol. 7, pp. 572–574.CrossRefGoogle Scholar
  21. 21.
    Kuznetsova, V.E., Vasiliskov, V.A., Zasedatelev, A.S., and Chudinov, A.V., Mend. Commun., 2008, vol. 18, no. 3, pp. 138–140.CrossRefGoogle Scholar
  22. 22.
    Chinchilla, R. and Najera, C., Chem. Soc. Rev., 2011, vol. 40, pp. 5084–5121.CrossRefPubMedGoogle Scholar
  23. 23.
    Seela, F. and Sirivolu, V.R., Helv. Chim. Acta, 2007, vol. 90, pp. 535–552.CrossRefGoogle Scholar
  24. 24.
    Dziuba, D., Pohl, R., and Hocek, M., Bioconjugate Chem., 2014, vol. 25, no. 11, pp. 1984–1995.CrossRefGoogle Scholar
  25. 25.
    Kozlov, M., Bergendahl, V., Burgess, R., Goldfarb, A., and Mustaev, A., Anal. Biochem., 2005, vol. 342, pp. 206–213.CrossRefPubMedGoogle Scholar
  26. 26.
    Gryadunov, D., Mikhailovich, V., Lapa, S., Roudinskii, N., Donnikov, M., Pan’kov, S., Markova, O., Kuz’min, A., Chernousova, L., Skotnikova, O., Moroz, A., Zasedatelev, A., and Mirzabekov, A., Clin. Microbiol. Infect., 2005, vol. 11, pp. 531–539.CrossRefPubMedGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • T. O. Guseinov
    • 1
  • V. E. Kuznetsova
    • 1
  • V. E. Shershov
    • 1
  • M. A. Spitsyn
    • 1
  • S. A. Lapa
    • 1
  • A. S. Zasedatelev
    • 1
  • A. V. Chudinov
    • 1
  1. 1.Engelhardt Institute of Molecular BiologyRussian Academy of SciencesMoscowRussia

Personalised recommendations

Cite article

Buy options