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New Photoreactive Cleavable Reagents with Trifluoromethyldiazirine Group

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Abstract

Photoreactive crosslinking reagents that simultaneously contain a trifluoromethyldiazirine and an o-nitrobenzyl groups were synthesized for the first time. Photochemical properties of the reagents were studied, and the possibility of separate activation of the diazirine group and o-nitrobenzyl linker was shown.

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References

  1. Singh, A., Thornton, E.R., and Westheimer, F.H., J. Biol. Chem., 1962, vol. 23, pp. 3006–3008.

    Google Scholar 

  2. Bayley, H., Photogenerated Reagents in Biochemistry and Molecular Biology, Work, T. and Burdon, R., Eds., Amsterdam: Elsevier, 1983, vol. 12, p. 187.

    Google Scholar 

  3. Brunner, J., Annu. Rev. Biochem., 1993, vol. 62, pp. 483–514.

    Google Scholar 

  4. Kotzyba-Hilbert, F., Kapfer, I., and Goedner, M., Angew. Chem., Int. Ed., 1995, vol. 34, pp. 1296–1312.

    Google Scholar 

  5. Brunner, J. and Richards, F., J. Biol. Chem., 1980, vol. 225, pp. 3319–3329.

    Google Scholar 

  6. Kogon, A.A., New Photoreactive Reagents for Studying Biological Macromoleculs by the Method of Fast Photoaffinity Crosslinking, Cand. Sc. (Chem.) Dissertation, Moscow: Moscow State Univ., 1990.

    Google Scholar 

  7. Savage, M.D., Mattson, G., Desai, S., Nielander, G.W., Morgensen, S., and Conklin, E.J., Avidin–Biotin Chemistry: a Handbook, Illinois: Pierce Chemical Co., 1992.

    Google Scholar 

  8. Kogon, A., Peletskaya, E., Quinn, T., and Folk, W., Abstracts of Papers, 37 Annual West Central States Biochemistry and Molecular Biology Conf., Research and Education, Univ. of Missouri, Columbia, 1994, p. 60.

  9. Brunner, J., Trends in Cell Biol., 1996, vol. 6, pp. 154–157.

    Google Scholar 

  10. Bochkarev, D. and Kogon, A., Anal. Biochem., 1992, vol. 204, pp. 90–95.

    Google Scholar 

  11. Kogon, A., Bochkarev, D., Baskunov, B., and Cherpakov, A., Liebigs Ann. Chem., 1992, pp. 879–881.

  12. Kempin, U., Kanoaka, Y., and Hatanaka, Y., Heterocycles, 1998, vol. 49, pp. 465–468.

    Google Scholar 

  13. Fang, K., Hashimoto, M., Jokush, S., Turro, N.J., and Nakanishi, K., J. Am. Chem. Soc., 1998, vol. 120, pp. 8543–8544.

    Google Scholar 

  14. Pillai, K., Synthesis, 1980, pp. 1–26.

  15. Lloyd-Williamsetal, F., Tetrahedron, 1993, vol. 49, pp. 11065–11133.

    Google Scholar 

  16. Olejnik, J., Krzymanska-Olejnik, E., and Rothschild, K.J., Nucleic Acids Res., 1998, vol. 26, pp. 3572–3576.

    Google Scholar 

  17. Wei, Y., Yan, Y., Pei, D., and Gong, B., Bioorg. Med. Chem. Letters, 1998, vol. 8, pp. 2419–2422.

    Google Scholar 

  18. Olejnik, J., Ludemann, H.-C., Krzymanska-Olejnik, E., Berkenkamp, S., Hillenkamp, F., and Rothschild, K.J., Nucleic Acids Res., 1999, vol. 27, pp. 4626–4631.

    Google Scholar 

  19. Nassal, M., Liebigs Ann. Chem., 1983, pp. 1510–1523.

  20. Nassal, M., J. Am. Chem. Soc., 1984, vol. 106, pp. 7540–7545.

    Google Scholar 

  21. Topin, A.N., Vestn. Mosk. Gos. Univ., Ser. 2: Khim., 1995, vol. 36, pp. 583–587.

    Google Scholar 

  22. Delepine, M., Compt. Rend., 1895, vol. 120, p. 501.

    Google Scholar 

  23. Tietze, L.F. and Eicher, T., Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Stuttgart: Georg Tieme, 1991. Translated under the title Preparativnaya organicheskaya khimiya, Moscow: Mir, 1999.

    Google Scholar 

  24. Angial, S., Organic Reactions, vol. 8, New York: John Wiley & Sons, 1954. Translated under the title Organicheskie reaktsii, Moscow: Inostrannaya Literatura, 1965, Sbornik 8, p. 263, London, Chapman&Hall.

    Google Scholar 

  25. Houben-Weyl, vol. XI, 1957, p. 106.

  26. Brunner, J. and Semenza, G., Biochemistry, 1981, vol. 20, pp. 7174–7182.

    Google Scholar 

  27. Dolder, M., Michel, H., and Sigrist, H., J. Protein Chem., 1990, vol. 9, pp. 407–415.

    Google Scholar 

  28. Wieboldt, R., Ramesh, D., Carpenter, B.K., and Hess, G.P., Biochemistry, 1994, vol. 33, pp. 1526–1533.

    Google Scholar 

  29. Brunner, J., Senn, H., and Richards, F.M., J. Biol. Chem., 1980, vol. 255, pp. 3313–3318.

    Google Scholar 

  30. Eksperimental'nye metody khimicheskoi kinetiki (Experimental Methods of Chemical Kinetics), Emanuel', N.M. and Sergeev, G.B., Eds., Moscow: Vysshaya Shkola, 1980, pp. 132–135.

    Google Scholar 

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Mchedlidze, M.T., Sumbatyan, N.V., Bondar', D.A. et al. New Photoreactive Cleavable Reagents with Trifluoromethyldiazirine Group. Russian Journal of Bioorganic Chemistry 29, 177–184 (2003). https://doi.org/10.1023/A:1023268617727

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