Back to Search Start Over

Enantioseparation and molecular modeling study of chiral amines as three naphthaldimine derivatives using amylose or cellulose trisphenylcarbamate chiral stationary phases.

Authors :
Adhikari S
Bhujbal S
Paik MJ
Lee W
Source :
Chirality [Chirality] 2023 Jan; Vol. 35 (1), pp. 29-39. Date of Electronic Publication: 2022 Nov 02.
Publication Year :
2023

Abstract

This study describes the enantioseparation of three chiral amines as naphthaldimine derivatives, using normal phase HPLC with amylose and cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phases (CSPs). Three chiral amines were derivatized using three structurally similar naphthaldehyde derivatizing agents, and the enantioselectivity of the CSPs toward the derivatives was examined. The degree of enantioseparation and resolution was affected by the amylose or cellulose-derived CSPs and aromatic moieties as well as a kind of chiral amine. Especially, efficient enantiomer separation was observed for 2-hydroxynapthaldimine derivatives on cellulose-derived CSPs. Molecular docking studies of three naphthaldimine derivatives of leucinol on cellulose tris(3,5-dimethylphenylcarbamate) were performed to estimate the binding energies and conformations of the CSP-analyte complexes. The obtained binding energies were in good agreement with the experimentally determined enantioseparation and elution order.<br /> (© 2022 Wiley Periodicals LLC.)

Details

Language :
English
ISSN :
1520-636X
Volume :
35
Issue :
1
Database :
MEDLINE
Journal :
Chirality
Publication Type :
Academic Journal
Accession number :
36323631
Full Text :
https://doi.org/10.1002/chir.23513