Binding modes identification through molecular dynamic simulations: A case study with carnosine enantiomers and the Teicoplanin A2-2-based chiral stationary phase.
binding modes
chiral chromatography
enantioseparation
molecular dynamics
teicoplanin
Journal
Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554
Informations de publication
Date de publication:
May 2020
May 2020
Historique:
received:
27
01
2020
revised:
25
02
2020
accepted:
26
02
2020
pubmed:
1
3
2020
medline:
14
1
2021
entrez:
1
3
2020
Statut:
ppublish
Résumé
In the present study, an in silico methodology able to define the binding modes adopted by carnosine enantiomers in the setting of the chiral recognition process is described. The inter- and intramolecular forces involved in the enantioseparation process with the Teicoplanin A2-2 chiral selector and carnosine as model compound are successfully identified. This approach fully rationalizes, at a molecular level, the (S) < (R) enantiomeric elution order obtained under reversed-phase conditions. Consistent explanations were achieved by managing molecular dynamics results with advanced techniques of data analysis. As a result, the time-dependent identification of all the interactions simultaneously occurring in the chiral selector-enantiomeric analyte binding process was obtained. Accordingly, it was found that only (R)-carnosine is able to engage a stabilizing charge-charge interaction through its ionized imidazole ring with the carboxylate counter-part on the chiral selector. Instead, (S)-carnosine establishes intramolecular contacts between its ionized functional groups, that limit its conformational freedom and impair the association with the chiral selector unit.
Identifiants
pubmed: 32112671
doi: 10.1002/jssc.202000092
doi:
Substances chimiques
teicoplanin A2
4U3D3YY81M
Teicoplanin
61036-62-2
Carnosine
8HO6PVN24W
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1728-1736Informations de copyright
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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