Ionspray (IS) and fast atom bombardment (FAB) positive ionization mass spectrometry (MS) of 1:1 β-cyclodextrin (β-CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 β-CD-MLT. Tandem MS collision-induced dissociation (CID) of such protonated 1:1 β-CD-MLT species showed the proton (charge) to be retained to a significant extent by the host and by its cage fragmentation products, in spite of the higher proton affinity of MLT with respect to that of β-CD. This requires an endothermic guest-to-host proton transfer to occur within the gaseous association. Collisional activation could be accounted for by the promotion of such an endothermic process; however, the proton affinity decrease of the guest determined by the loss of the elements of acetamide, which is a dominant MS dissociation reaction of pure protonated MLT, could also provide a rationale for such an endothermic guest-to-host proton transfer. This proposal parallels the reaction scheme we had previously formulated for the analogous MS and tandem MS behaviour of 1:1 β-CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright © 2001 John Wiley & Sons, Ltd.

Bongiorno, D., Ceraulo, L., Mele, A., Panzeri, W., Selva, A., & Liveri, V. (2001). Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry. JOURNAL OF MASS SPECTROMETRY, 36(11), 1189-1194 [10.1002/jms.226].

Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry

BONGIORNO, David;CERAULO, Leopoldo;
2001

Abstract

Ionspray (IS) and fast atom bombardment (FAB) positive ionization mass spectrometry (MS) of 1:1 β-cyclodextrin (β-CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 β-CD-MLT. Tandem MS collision-induced dissociation (CID) of such protonated 1:1 β-CD-MLT species showed the proton (charge) to be retained to a significant extent by the host and by its cage fragmentation products, in spite of the higher proton affinity of MLT with respect to that of β-CD. This requires an endothermic guest-to-host proton transfer to occur within the gaseous association. Collisional activation could be accounted for by the promotion of such an endothermic process; however, the proton affinity decrease of the guest determined by the loss of the elements of acetamide, which is a dominant MS dissociation reaction of pure protonated MLT, could also provide a rationale for such an endothermic guest-to-host proton transfer. This proposal parallels the reaction scheme we had previously formulated for the analogous MS and tandem MS behaviour of 1:1 β-CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright © 2001 John Wiley & Sons, Ltd.
Bongiorno, D., Ceraulo, L., Mele, A., Panzeri, W., Selva, A., & Liveri, V. (2001). Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry. JOURNAL OF MASS SPECTROMETRY, 36(11), 1189-1194 [10.1002/jms.226].
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10447/243606
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