Single isomer cyclodextrins as chiral selectors in capillary electrophoresis

被引:53
作者
Fejos, Ida [1 ]
Kalydi, Eszter [1 ,2 ]
Malanga, Milo [2 ]
Benkovics, Gabor [2 ]
Beni, Szabolcs [1 ]
机构
[1] Semmelweis Univ, Dept Pharmacognosy, Ulloi Ut 26, H-1085 Budapest, Hungary
[2] Cyclodextrin R&D Ltd, CYCLOLAB, Illatos Ut 7, H-1097 Budapest, Hungary
关键词
Capillary electrophoresis; Synthesis of single isomer cyclodextrin derivatives; Chiral separation; Enantiomer migration order; Enantiorecognition; Supramolecular interactions; NUCLEAR-MAGNETIC-RESONANCE; SULFATED BETA-CYCLODEXTRIN; DANSYL AMINO-ACIDS; POSITIVELY CHARGED CYCLODEXTRINS; ENANTIOMER MIGRATION ORDER; PH BACKGROUND ELECTROLYTE; CLICKED AC REGIOISOMER; ZONE-ELECTROPHORESIS; GAMMA-CYCLODEXTRIN; RESOLVING AGENT;
D O I
10.1016/j.chroma.2020.461375
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Since decades, cyclodextrins are one of the most powerful selectors in chiral capillary electrophoresis for the enantioseparation of diverse organic compounds. This review concerns papers published over the last decade (from 2009 until nowadays), dealing with the capillary electrophoretic application of single isomer cyclodextrin derivatives in chiral separations. Following a brief overview of their synthetic approaches, the inventory of the neutral, negatively and positively charged (including both permanently ionic and pH-tunable ionizable substituents) and zwitterionic CD derivatives is presented, with insights to underlying structural aspects by NMR spectroscopy and molecular modeling. CE represents an ideal tool to study the weak, non-covalent supramolecular interactions. The published methods are reviewed in the light of enantioselectivity, enantiomer migration order and the fine-tuning of enantiodiscrimination by the substitution pattern of the single entity selector molecules, which is hardly possible for their randomly substituted counterparts. All the reviewed publications herein support that cyclodextrin-based chiral capillary electrophoresis seems to remain a popular choice in pharmaceutical and biomedical analysis. (c) 2020 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY-NC-ND license. (http://creativecommons.org/licenses/by-nc-nd/4.0/)
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页数:30
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