Abstract

European Journal of Mass Spectrometry
Volume 15 Issue 2, Pages 199–208 (2009)
doi: 10.1255/ejms.968

Gas-phase ion chemistry of protonated melatonin

David Bongiorno,^a Leopoldo Ceraulo,^a,* Lorenzo Camarda,^a Maurizio Ciofalo,^b Mirella Ferrugia,^a Serena Indelicato,^a Andrea Mele^c and Vincenzo Turco Liveri^d
aDipartimento di Chimica e Tecnologie Farmaceutiche, Università di Palermo, Via Archirafi 32, I-90123 Palermo, Italy. E-mail: lceraulo@unipa.it
^bDipartimento di Ingegneria e Tecnologie Agro-Forestali, Sezione di Chimica, Università di Palermo, Viale delle Scienze, Edificio 4, I-90128 Palermo, Italy
^cDipartimento di Chimica, Materiali ed Ingegneria Chimica “G. Natta”–Politecnico di Milano, Via Mancinelli 7, I-20131, Milano, Italy
^dDipartimento di Chimica Fisica “F. Accascina”, Università di Palermo, Viale delle Scienze-Parco d’Orleans II, I-90128, Palermo, Italy

The gas-phase ion chemistry of protonated melatonin has been investigated by mass spectrometric (MS) techniques involving chemical ionisation, fast atom bombardment and electrospray ionisation. Either naturally-occurring or collision-induced decomposition e–D derivatives obtained by exchange with D₂O. The analysis of experimental results allows definite pathways for the formation of the ion at m/z 174 to be assigned and sheds some more light on the overall fragmentation pathways. Experiments on labelled derivatives evidenced H–D scrambling processes during fragmentation.

Keywords: melatonin, ESI/MS, ESI/MS/MS, deuterium labelled compounds, ion chemistry, scrambling reactions, proton affinity

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