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
Ulrich WoiwodeMichael Lämmerhofer

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 ...Continue Reading

References

Feb 7, 1997·Journal of Chromatography. B, Biomedical Sciences and Applications·K Fried, I W Wainer
Feb 24, 2001·Journal of Chromatography. a·N M MaierW Lindner
Mar 24, 2009·Journal of Separation Science·Róbert BerkeczAntal Péter
Jan 27, 2015·Journal of Pharmaceutical and Biomedical Analysis·Federica IanniBenedetto Natalini
Nov 21, 2016·Analytical and Bioanalytical Chemistry·Miguel Peñín-IbáñezLuis María Polo-Díez
Dec 10, 2016·Analytical Chemistry·Dwight R Stoll, Peter W Carr
Feb 15, 2017·Analytical Chemistry·Chandan L BarhateChristopher J Welch
Aug 16, 2017·Journal of Chromatography. a·Ravindra Suryakant HegadeFrederic Lynen

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Citations

Mar 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana TeixeiraCarla Fernandes
Jul 17, 2020·Amino Acids·Giacomo CarenziLoredano Pollegioni
Jan 3, 2021·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Xue-Jiao ZhaoZhao-Ying Liu

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