The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions

Schmidt J, Kuck D, Franke K, Sultani H, Laub A, Wessjohann LA (2019)
JOURNAL OF MASS SPECTROMETRY 54(6): 549-556.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Long-chain ferulic acid esters, such as eicosyl ferulate (1), show a complex and analytically valuable fragmentation behavior under negative ion electrospay collision-induced dissociation ((-)-ESI-CID) mass spectrometry, as studied by use of a high-resolution (Orbitrap) mass spectrometer. In a strong contrast to the very simple fragmentation of the [M + H](+) ion, which is discussed briefly, the deprotonated molecule, [M - H](-), exhibits a rich secondary fragmentation chemistry. It first loses a methyl radical (MS2) and the ortho-quinoid [M - H - Me](-center dot) radical anion thus formed then dissociates by loss of an extended series of neutral radicals, CnH2n + 1 center dot (n = 0-16) from the long alkyl chain, in competition with the expulsion of CO and CO2 (MS3). The further fragmentation (MS4) of the [M - H - Me - C3H7](-) ion, discussed as an example, and the highly specific losses of alkyl radicals from the [M - H - Me - CO](-center dot) and [M - H - Me - CO2](-center dot) ions provide some mechanistic and structural insights.
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Zeitschriftentitel
JOURNAL OF MASS SPECTROMETRY
Band
54
Ausgabe
6
Seite(n)
549-556
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Schmidt J, Kuck D, Franke K, Sultani H, Laub A, Wessjohann LA. The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions. JOURNAL OF MASS SPECTROMETRY. 2019;54(6):549-556.
Schmidt, J., Kuck, D., Franke, K., Sultani, H., Laub, A., & Wessjohann, L. A. (2019). The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions. JOURNAL OF MASS SPECTROMETRY, 54(6), 549-556. doi:10.1002/jms.4357
Schmidt, J., Kuck, D., Franke, K., Sultani, H., Laub, A., and Wessjohann, L. A. (2019). The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions. JOURNAL OF MASS SPECTROMETRY 54, 549-556.
Schmidt, J., et al., 2019. The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions. JOURNAL OF MASS SPECTROMETRY, 54(6), p 549-556.
J. Schmidt, et al., “The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions”, JOURNAL OF MASS SPECTROMETRY, vol. 54, 2019, pp. 549-556.
Schmidt, J., Kuck, D., Franke, K., Sultani, H., Laub, A., Wessjohann, L.A.: The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions. JOURNAL OF MASS SPECTROMETRY. 54, 549-556 (2019).
Schmidt, Juergen, Kuck, Dietmar, Franke, Katrin, Sultani, Haider, Laub, Annegret, and Wessjohann, Ludger A. “The unusual fragmentation of long-chain feruloyl esters under negative ion electrospray conditions”. JOURNAL OF MASS SPECTROMETRY 54.6 (2019): 549-556.

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