Identification and interconversion of diastereomeric oligo-Troger bases probed by ion mobility mass spectrometry

0379208 - ÚOCHB 2013 RIV GB eng J - Journal Article
Révész, Agnes - Schröder, Detlef - Rokob, Tibor András - Havlík, M. - Dolenský, B.
Identification and interconversion of diastereomeric oligo-Troger bases probed by ion mobility mass spectrometry.
Physical Chemistry Chemical Physics. Roč. 14, č. 19 (2012), s. 6987-6995. ISSN 1463-9076. E-ISSN 1463-9084
Grant - others:GA ČR(CZ) GA203/08/1445; European Research Council(XE) AdG HORIZOMS
Institutional research plan: CEZ:AV0Z40550506
Keywords : cross section * epimerization * ion mobility * mass spectrometry * Troeger bases
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 3.829, year: 2012

Oligo-Troger bases are auspicious scaffolds of molecular engineering, which motivates studies on the mechanism of their interconversion and on the facile determination of the relative configuration of their diastereoisomers. Protonated, sodiated, and argentated species of those compounds were therefore studied via ion-mobility mass spectrometry (IM-MS), allowing differentiation on the basis of the shapes of the ions. First, the isomerization was confirmed to be acid-catalyzed as it takes place readily in the case of protonated Troger bases, whereas the metallated bases are configurationally stable. Second, the corrected arrival times of the various isomers of the cationized bases were found to show distinct differences in IM-MS, and their excellent correlation with the cross sections obtained from quantum chemical calculations paves the way toward the easy identification of diastereoisomers.
Permanent Link: http://hdl.handle.net/11104/0210468