Gas-phase interactions of organotin compounds with cysteine.

Autor: Latrous L; Laboratoire de Chimie Analytique et Electrochimie Campus Universitaire, Faculté des Sciences de Tunis, Université de Tunis El Manar, 2092, Tunis, Tunisia. latifa.latrous@ipeiem.rnu.tn., Salpin JY; Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement, Université d'Evry Val d'Essonne, Bâtiment Maupertuis-Boulevard François Mitterrand, 91025, Evry, France.; CNRS-UMR 8587, Evry, France., Haldys V; Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement, Université d'Evry Val d'Essonne, Bâtiment Maupertuis-Boulevard François Mitterrand, 91025, Evry, France.; CNRS-UMR 8587, Evry, France., Léon E; Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement, Université d'Evry Val d'Essonne, Bâtiment Maupertuis-Boulevard François Mitterrand, 91025, Evry, France.; CNRS-UMR 8587, Evry, France., Correia C; Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement, Université d'Evry Val d'Essonne, Bâtiment Maupertuis-Boulevard François Mitterrand, 91025, Evry, France.; CNRS-UMR 8587, Evry, France., Lamsabhi AM; Departamento de Química, Ciencias, M-13, Universidad Autónoma de Madrid, Campus de Excelencia UAM-CSIC Cantoblanco, 28049, Madrid, Spain.
Jazyk: angličtina
Zdroj: Journal of mass spectrometry : JMS [J Mass Spectrom] 2016 Nov; Vol. 51 (11), pp. 1006-1015.
DOI: 10.1002/jms.3812
Abstrakt: The gas-phase interactions of cysteine with di-organotin and tri-organotin compounds have been studied by mass spectrometry experiments and quantum calculations. Positive-ion electrospray spectra show that the interaction of di- and tri-organotins with cysteine results in the formation of [(R) 2 Sn(Cys-H)] + and [(R) 3 Sn(Cys)] + ions, respectively. MS/MS spectra of [(R) 2 Sn(Cys-H)] + complexes are characterized by numerous fragmentation processes, notably associated with elimination of NH 3 and (C,H 2 ,O 2 ). Several dissociation routes are characteristic of each given organic species. Upon collision, both the [(R) 3 Sn(Gly)] + and [(R) 3 Sn(Cys)] + complexes are associated with elimination of the intact amino acid, leading to the formation of [(R) 3 Sn] + cation. But for the latter complex, two additional fragmentation processes are observed, associated with the elimination of NH 3 and C 3 H 4 O 2 S. Calculations indicate that the interaction between organotins and cysteine is predominantly electrostatic but also exhibits a considerable covalent character, which is slightly more pronounced in tri-organotin complexes. A preferred bidentate interaction of the type -η 2 -S-NH 2 , with sulfur and the amino group, is observed. As for the [(R) 3 Sn(Cys)] + complexes, their stability is due to the combination of the hydrogen bond taking place between the amino group and the sulfur lone pair and the interaction between the carboxylic oxygen atom and the metal. Copyright © 2016 John Wiley & Sons, Ltd.
(Copyright © 2016 John Wiley & Sons, Ltd.)
Databáze: MEDLINE
Externí odkaz:
Nepřihlášeným uživatelům se plný text nezobrazuje