Complementary enantioselectivity profiles of chiral cinchonan carbamate selectors with distinct carbamate residues and their implementation in enantioselective two-dimensional high-performance liquid chromatography of amino acids

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Woiwode , U , Ferri , M , Maier , N M , Lindner , W & Lämmerhofer , M 2018 , ' Complementary enantioselectivity profiles of chiral cinchonan carbamate selectors with distinct carbamate residues and their implementation in enantioselective two-dimensional high-performance liquid chromatography of amino acids ' , Journal of Chromatography. A , vol. 1558 , pp. 29-36 . https://doi.org/10.1016/j.chroma.2018.04.061

Title: Complementary enantioselectivity profiles of chiral cinchonan carbamate selectors with distinct carbamate residues and their implementation in enantioselective two-dimensional high-performance liquid chromatography of amino acids
Author: Woiwode, Ulrich; Ferri, Martina; Maier, Norbert M.; Lindner, Wolfgang; Lämmerhofer, Michael
Contributor: University of Helsinki, Department of Chemistry
Date: 2018-07-13
Language: eng
Number of pages: 8
Belongs to series: Journal of Chromatography. A
ISSN: 0021-9673
URI: http://hdl.handle.net/10138/314406
Abstract: Abstract A cardinal requirement for effective 2D-HPLC separations is sufficient complementarity in the retention profiles of first and second dimension separations. It is shown that retention and enantioselectivity of chiral selectors derived from cinchona alkaloids can be conveniently modulated by structural variation of the carbamate residue of the quinine/quinidine carbamate ligand of such chiral stationary phases (CSP). A variety of aliphatic and aromatic residues have been tested in comparison to non-carbamoylated quinine CSP. Various measures of orthogonality have been utilized to derive the CSP that is most complementary to the tert-butylcarbamoylated quinine CSP (tBuCQN CSP), which is commercially available as Chiralpak QN-AX column. It turned out that O-9-(2,6-diisopropylphenylcarbamoyl)-modified quinine is most promising in this respect. Its implementation as a complementary CSP for the separation of amino acids derivatized with Sanger’s reagent (2,4-dinitrophenylated amino acids) in the first dimension combined with a tBuCQN CSP in the second dimension revealed successful enantiomer separations in a comprehensive chiral×chiral 2D-HPLC setup. However, the degree of complementarity could be greatly enhanced when simultaneously the absolute configurations were exchanged from quinine to quinidine in the chiral selector of the first dimension separation resulting in opposite elution orders of the enantiomers in the two dimensions. The advantage of such a chiral×chiral over achiral×chiral 2D-HPLC setup, amongst others, is the perfect compatibility of the mobile phase because in both dimensions the identical eluent can be used.
Subject: Multidimensional HPLC separations
chiral stationary phase
quinine
quinidine
amino acids
two-dimensional chromatography
RECOGNITION
STRATEGY
STATIONARY PHASES
RESOLUTION
Chiral stationary phase
Amino acids
ANION-EXCHANGERS
Quinine
ENANTIOSEPARATION
Two-dimensional chromatography
Quinidine
QUININE
SEPARATION
DERIVATIVES
HPLC
116 Chemical sciences
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