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Protonation-Induced Chirality Drives Separation by Differential Ion Mobility Spectrometry
Christian Ieritano1,2,3, J C Yves Le Blanc4, Bradley B Schneider4
1Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, ON, N2L 3G1, Canada.
Angewandte Chemie (International Ed. in English)
|December 28, 2021
Summary
Protonation of Verapamil creates a new chiral center, leading to two distinct ions detectable by differential mobility spectrometry (DMS). This protonation-induced chirality is a common phenomenon in chiral amines.
Area of Science:
- Analytical Chemistry
- Organic Chemistry
- Physical Chemistry
Background:
- Verapamil analysis using differential mobility spectrometry (DMS) revealed an unusual ionogram with two peaks.
- Metabolites of Verapamil exhibited single peaks, highlighting Verapamil's unique behavior.
Purpose of the Study:
- To investigate the cause of the dual-peak ionogram observed for protonated Verapamil.
- To explore the phenomenon of protonation-induced chirality in amines using DMS.
Main Methods:
- Development of a DMS workflow for analyzing Verapamil and its metabolites.
- Analysis of protonated Verapamil and 12 other chiral amines using DMS.
Main Results:
- Protonation of Verapamil's tertiary amine generated a stereogenic quaternary amine, introducing a new chiral center.
- The protonated Verapamil ion existed as four stereochemical configurations, forming two diastereomeric pairs resolvable by DMS.
- Protonation-induced diastereomers were successfully resolved for 12 additional chiral amines, confirming a general phenomenon.
Conclusions:
- Protonation can induce chirality in achiral or chiral amines, creating diastereomers.
- DMS is a powerful technique for resolving protonation-induced diastereomers of chiral amines.
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