Skip to main content
SpringerLink
Log in

New acid photogenerators based on thioxanthen-9-one sulfonium derivatives for detritylation in the oligonucleotide synthesis

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Photochemical activity of a number of cationic thioxanthen-9-one derivatives for the formation of the trityl cation was studied, which resulted in the selection of compounds suitable for photodetritylation. 10-(4-Heptyloxyphenyl)-9-oxo-2-(N,N,N-triethylammonio)methyl-9H-thioxanthenium bis(hexafluorophosphate) and 2-methyl-, 2-(2-methyl-1-propanoyl-2-tosyl)-, 1-chloro-4-propoxy-, and 2,4-diethyl-10-(4-heptyloxyphenyl)-9-oxo-9H-thioxanthenium hexafluorophosphates were found to be photoactivators of detritylation of 5′-O-(4,4′-dimethoxytrityl)thymidine. The detritylation reaction is the most efficient in dichloromethane. 2,4-Diethyl-10-(4-heptyloxyphenyl)-9-oxo-9H-thioxanthenium hexafluorophosphate was used as a detritylation photoactivator in the oligonucleotide synthesis using an automated DNA synthesizer. The yield in the elongation step of the oligonucleotide chain was 98%.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J. Cello, A. V. Paul, E. Wimmer, Science, 2002, 297, 1016.

    Article  CAS  Google Scholar 

  2. H. O. Smith, C. A. Hutchison, C. Pfannkoch, J. C. Venter, Proc. Nat. Acad. Sci., 2003, 100, 15440.

    Article  CAS  Google Scholar 

  3. D. G. Gibson, J. I. Glass, C. Lartigue, V. N. Noskov, R. Y. Chuang, M. A. Algire, G. A. Benders, M. G. Montague, L. Ma, M. M. Moodie, C. Merryman, S. Vashee, R. Krishnakumar, N. Assad-Garcia, C. Andrews-Pfannkoch, E. A. Denisova, L. Young, Z. Q. Qi, T. H. Segall-Shapiro, C. H. Calvey, P. P. Parmar, C. A. Hutchison, H. O. Smith, J. C. Venter, Science, 2010, 329, 52.

    Article  CAS  Google Scholar 

  4. G. M. Church, Scientific Am., 2006, No. 1, 47.

  5. A. Y. Borovkov, A. V. Loskutov, M. D. Robida, K. M. Day, J. A. Cano, T. L. Olson, H. Patel, K. Brown, P. D. Hunter, K. F. Sykes, Nucleic Acids Research, 2010, 38, No. 19, 180.

    Article  Google Scholar 

  6. M. A. Russell, A. P. Laws, J. H. Atherton, M. I. Page, Org. Biomol. Chem., 2009, 7, 52.

    Article  CAS  Google Scholar 

  7. L. I. McBride, M. H. Caruthers, Tetrahedron Lett., 1983, 24, 245.

    Article  CAS  Google Scholar 

  8. S. L. Beaucage, M. H. Caruthers, Tetrahedron Lett., 1981, 22, 1859.

    Article  CAS  Google Scholar 

  9. X. Gao, P. Yu, E. Le Proust, L. Sonigo, J. P. Pellois, H. Zhang, J. Am. Chem. Soc., 1998, 120, 12698.

    Article  CAS  Google Scholar 

  10. X. Gao, E. Le Proust, H. Zhang, O. Srivannavit, E. Gulari, P. Yu, C. Nishiguchi, Q. Xiang, X. Zhou, Nucleic Acids Res., 2001, 29, 4744.

    Article  CAS  Google Scholar 

  11. P. J. Serafinowski, P. B. Garland, J. Am. Chem. Soc., 2003, 125, 962.

    Article  CAS  Google Scholar 

  12. P. J. Serafinowski, P. B. Garland, Org. Biomol. Chem., 2008, 6, 3284.

    Article  CAS  Google Scholar 

  13. V. A. Loskutov, V. A. Shelkovnikov, Zh. Org. Khim., 2006, 42, 1113 [Russ. J. Org. Chem. (Engl. Transl.), 2006, 42, 298].

    Google Scholar 

  14. V. A. Loskutov, V. A. Shelkovnikov, Zh. Org. Khim., 2006, 42, 313 [Russ. J. Org. Chem. (Engl. Transl.), 2006, 42, 1097].

    Google Scholar 

  15. J. V. Crivello, J. Pol. Sci.: Part A: Pol. Chem., 1999, 37, 4241.

    Article  CAS  Google Scholar 

  16. J. V. Crivello, J. H. W. Lam, J. Pol. Sci.: Part A: Pol. Chem., 1996, 34, 3231.

    Article  CAS  Google Scholar 

  17. S. Mahajan, B. Vaijayanthi, G. Rembhotkar, K. C. Gupta, P. Kumar, Methods Mol. Biol., 2007, 381, 165.

    Article  CAS  Google Scholar 

  18. M. A. Russell, A. P. Laws, J. H. Atherton, M. I. Page, Org. Biomol. Chem., 2009, 7, 52.

    Article  CAS  Google Scholar 

  19. Eksperimental’nye metody khimicheskoi kinetiki [Experimental Methods of Chemical Kinetics], Eds N. M. Emanuel’, M. G. Kuz’min, MGU, Moscow, 1985, 384 pp. (in Russian).

    Google Scholar 

  20. G. M. Panchenkov, V. P. Lebedev, Khimicheskaya kinetika i kataliz [Chemical Kinetics and Catalysis], MGU, Moscow, 1961, 552 pp. (in Russian).

    Google Scholar 

  21. V. E. Kogan, G. S. Zenin, N. V. Penkina, Fizicheskaya khimiya. Ch. 2. Khimicheskaya kinetika: Uchebnoe posobie [Physical Chemistry. Part 2. Chemical Kinetics: Textbook], SZTU, SPb, 2005, 227 pp. (in Russian).

    Google Scholar 

  22. R. M. C. Dawson, D. C. Elliott, W. H. Elliott, K. M. Jones, Data for Biochemical Research, 3rd ed., Oxford Science Publications, OUP, Oxford, 1986, 580 pp.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    V. V. Shelkovnikov, V. A. Loskutov, E. V. Vasil’ev & N. V. Shekleina

  2. Research Educational Center “Molecular Design and Environmentally Safe Technologies”, Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    E. V. Vasil’ev

  3. Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 8 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    V. A. Ryabinin & A. N. Sinyakov

Authors
  1. V. V. Shelkovnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Loskutov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Vasil’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Shekleina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. A. Ryabinin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. N. Sinyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Vasil’ev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 548–556, March, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shelkovnikov, V.V., Loskutov, V.A., Vasil’ev, E.V. et al. New acid photogenerators based on thioxanthen-9-one sulfonium derivatives for detritylation in the oligonucleotide synthesis. Russ Chem Bull 60, 561–569 (2011). https://doi.org/10.1007/s11172-011-0087-x

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0087-x

Key words

Search

Navigation