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Tandem high-resolution electrospray ionization mass spectrometry of fluorinated thevinols and 18,19-dihydrothevinols

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Abstract

Fragmentation of fluorinated 18,19-dihydrothevinols and thevinols under electrospray ionization with collisionally activated dissociation accompanied by the elimination of an amine fragment from the cycle and the subsequent loss of H2O and CH3OH have been studied. For thevinol derivatives with a double bond at C18=C19, the [M + H]+ ions undergo the retro-Diels–Alder fragmentation, the abundance of which depends on substituents at the nitrogen and C20 atoms. The retro-Diels–Alder fragmentation of the [M + H]+ ions of thevinols bearing–CH3,–CH2CH=CH2, and \( - C{H_2} - \triangleleft \) groups at the nitrogen atom occurs due to the formation of a protonated diene molecule, whereas the elimination of a neutral diene in thevinols with hydrogen at the nitrogen atom has been observed.

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References

  1. McLuckey, S.A., J. Am. Soc. Mass Spectrom., 1992, vol. 3, no. 6, p. 599.

    Article  CAS  Google Scholar 

  2. Mass Spectrometry Handbook, Lee, M.S., Ed., New York: Wiley, 2012.

  3. Methods in Enzymology, vol. 402: Biological Mass Spectrometry, Burlingame, A.L., Ed., San Diego and London: Elsevier, 2005

  4. Kadentsev, V.I., Chizhov, A.O., Chizhov, O.S., Krupinova, O.N., Rzheznikov, V.M., and Golubovskaya, L.E., Eur. J. Mass Spectrom., 2006, vol. 12, no. 1, p. 75.

    Article  CAS  Google Scholar 

  5. Kadentsev, V.I., Chizhov, A.O., Chizhov, O.S., Kolotyrkina, N.G., Kutin, A.A., Nesterov, I.D., Chuvylkin, N.D., Rzheznikov, V.D., and Golubovskaya, L.E., Eur. J. Mass Spectrom., 2007, vol. 13, no. 1, p. 207.

    Article  CAS  Google Scholar 

  6. Kadentsev, V.I., Chizhov, A.O., Chizhov, O.S., Kolotyrkina, N.G., Kutin, A.A., Rzheznikov, V.M., and Golubovskaya, L.E., Izv. Akad. Nauk, Ser.: Khim., 2008, no. 3, p. 92.

    Google Scholar 

  7. Kadentsev, V.I., Chizhov, A.O., Kolotyrkina, N.G., Vesela, I.V., and Kamernitskii, A.V., Mass-Spektrometria, 2008, vol. 5, no. 3, p. 219.

    CAS  Google Scholar 

  8. Kadentsev, V.I., Chizhov, A.O., Chizhov, O.S., and Voznyi, Ya.V., Mass-Spektrometria, 2008, vol. 5, no. 1, p. 45.

    CAS  Google Scholar 

  9. Kadentsev, V.I., Chizhov, A.O., Chizhov, O.S., and Voznyi, Ya.V., Mass-Spektrometria, 2008, vol. 5, no. 1, p. 39.

    CAS  Google Scholar 

  10. Moiseev, S.K., Kalinin, V.N., and Sandulenko, I.V., RF Patent 2506265, 2014.

    Google Scholar 

  11. Belyakov, P.A., Kadentsev, V.I., Chizhov, A.O., Kolotyrkina, N.G., Shashkov, A.S., and Ananikov, V.P., Mendeleev Commun., 2010, vol. 20, no. 3, p. 125.

    Article  CAS  Google Scholar 

  12. Brenton, A.G. and Godfrey, A.R., J. Am. Soc. Mass Spectrom., 2010, vol. 21, no. 11, p. 1821.

    CAS  Google Scholar 

  13. Musharraf, S.G., Goher, M., Shahnaz, S., Choudhary, M.I., and Atta-ur-Rahman, Rapid Commun. Mass Spectrom., 2013, vol. 27, no. 1, p. 169.

    Article  CAS  Google Scholar 

  14. Solov’ev, A.A., Kadentsev, V.I., and Chizhov, O.S., Usp. Khim., 1979, vol. 48, no. 7, p. 1180.

    Google Scholar 

  15. Delcambre, A. and Saucier, C., J. Mass Spectrom., 2012, vol. 47, no. 6, p. 727.

    Article  CAS  Google Scholar 

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Correspondence to D. B. Eremin.

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Original Russian Text © D.B. Eremin, V.I. Kadentsev, I.V. Sandulenko, S.K. Moiseev, 2014, published in Mass-spektrometriya, 2014, Vol. 11, No. 3, pp. 163–168.

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Eremin, D.B., Kadentsev, V.I., Sandulenko, I.V. et al. Tandem high-resolution electrospray ionization mass spectrometry of fluorinated thevinols and 18,19-dihydrothevinols. J Anal Chem 70, 1561–1568 (2015). https://doi.org/10.1134/S1061934815130031

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  • DOI: https://doi.org/10.1134/S1061934815130031

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