期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 9, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202116794
关键词
Chiral Derivatization; Diastereomer; Ion Mobility; Mass Spectrometry; Verapamil
资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Ontario Centres of Excellence
- government of Ontario
- InnoHK initiative
- Hong Kong Special Administrative Region Government
- Government of Canada through the Vanier Canada Graduate Scholarship
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [449651261]
- NSERC Undergraduate Student Research Award (USRA)
- National Institutes of Health [R01-GM129325]
- Office of Cyber Infrastructure and Computational Biology, National Institute of Allergy and Infectious Diseases
A workflow was developed to analyze Verapamil and its metabolites, and it was observed that the ionogram of protonated Verapamil had two peaks while the metabolites had only one peak. This was attributed to the protonation at the tertiary amino moiety of Verapamil, which generated a chiral quaternary amine.
Upon development of a workflow to analyze (+/-)-Verapamil and its metabolites using differential mobility spectrometry (DMS), we noticed that the ionogram of protonated Verapamil consisted of two peaks. This was inconsistent with its metabolites, as each exhibited only a single peak in the respective ionograms. The unique behaviour of Verapamil was attributed to protonation at its tertiary amino moiety, which generated a stereogenic quaternary amine. The introduction of additional chirality upon N-protonation of Verapamil renders four possible stereochemical configurations for the protonated ion: (R,R), (S,S), (R,S), or (S,R). The (R,R)/(S,S) and (R,S)/(S,R) enantiomeric pairs are diastereomeric and thus exhibit unique conformations that are resolvable by linear and differential ion mobility techniques. Protonation-induced chirality appears to be a general phenomenon, as N-protonation of 12 additional chiral amines generated diastereomers that were readily resolved by DMS.
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