Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

被引:77
作者
Peluso, Paola [1 ]
Chankvetadze, Bezhan [2 ]
机构
[1] CNR, Ist Chim Biomol ICB, Sedesecondaria Sassari, Traversa Crucca 3, Sassari, Italy
[2] Tbilisi State Univ, Inst Phys & Analyt Chem, Sch Exact & Nat Sci, Chavchavadze Ave 1, Tbilisi 0179, Georgia
基金
美国国家科学基金会;
关键词
Capillary electrophoresis; Computational methods; Cyclodextrins; Enantioseparation; Molecular modeling; NUCLEAR-MAGNETIC-RESONANCE; ENANTIOMER MIGRATION ORDER; CARBOXYMETHYL-BETA-CYCLODEXTRIN; HIGH-ENERGY WATER; INCLUSION COMPLEXES; CRYSTAL-STRUCTURE; ELECTROKINETIC CHROMATOGRAPHY; ZONE-ELECTROPHORESIS; ALPHA-CYCLODEXTRIN; GAMMA-CYCLODEXTRIN;
D O I
10.1002/elps.202100053
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
CDs are cyclic oligosaccharides consisting of alpha-d-glucopyranosyl units linked through 1,4-linkages, which are obtained from enzymatic degradation of starch. The coexistence of hydrophilic and hydrophobic regions in the same structure makes these macrocycles extremely versatile as complexing host with application in food, cosmetics, environmental, agriculture, textile, pharmaceutical, and chemical industries. Due to their inherent chirality, CDs have been also successfully used as chiral selectors in enantioseparation science, in particular, for CE enantioseparations. In the last decades, multidisciplinary approaches based on CE, NMR spectroscopy, X-ray crystallography, microcalorimetry, and molecular modeling have shed light on some aspects of recognition mechanisms underlying enantiodiscrimination. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a useful tool to model at molecular level the dynamics of diastereomeric associate formation to sample low-energy conformations, the binding energies between the enantiomer and the CD, and to profile noncovalent interactions contributing to the stability of CD/enantiomer association. On this basis, the aim of this review is to provide the reader with a critical overview on the applications of CDs in CE. In particular, the contemporary theory of the electrophoretic technique and the main structural features of CDs are described, with a specific focus on techniques, methods, and approaches to model CE enantioseparations promoted by native and substituted CDs. A systematic compilation of all published literature has not been attempted.
引用
收藏
页码:1676 / 1708
页数:33
相关论文
共 50 条
[41]   Determination of enantiomerization barrier of thioridazine by dynamic capillary electrophoresis using sulfated cyclodextrins as chiral selectors [J].
Lin, Ching-Erh ;
Ko, Ting-Chang ;
Kuo, Chia-Ming ;
Trapp, Oliver ;
Lin, Wann-Yin ;
Lin, Chen-Hsing ;
Wu, Jong-Chang ;
Liu, Yu-Chih .
ELECTROPHORESIS, 2009, 30 (17) :3071-3078
[42]   Chiral separation of tramadol enantiomers by capillary electrophoresis using cyclodextrins as chiral selectors and experimental design method optimization [J].
Sarkany, Anita ;
Hancu, Gabriel ;
Carje, Anca ;
Dragut, Claudiu ;
Papp, Lajos Attila .
CHEMICAL PAPERS, 2019, 73 (09) :2363-2370
[43]   Chiral separation of tramadol enantiomers by capillary electrophoresis using cyclodextrins as chiral selectors and experimental design method optimization [J].
Anita Sarkany ;
Gabriel Hancu ;
Anca Cârje ;
Claudiu Drăguț ;
Lajos Attila Papp .
Chemical Papers, 2019, 73 :2363-2370
[44]   Development of a Chiral Capillary Electrophoresis Method for the Enantioseparation of Verapamil Using Cyclodextrins as Chiral Selectors and Experimental Design Optimization [J].
Carcu-Dobrin, Melania ;
Hancu, Gabriel ;
Papp, Lajos Attila ;
Fulop, Ibolya ;
Kelemen, Hajnal .
SYMMETRY-BASEL, 2021, 13 (11)
[45]   Enantioseparations of dansyl amino acids by capillary electrophoresis using Cu(II) complexes with L-amino acylamides as chiral selectors in electrolytes [J].
Chen, ZL ;
Niitsuma, M ;
Nakagama, T ;
Uchiyama, K ;
Hobo, T .
JOURNAL OF SEPARATION SCIENCE, 2002, 25 (15-17) :1197-1201
[46]   Chiral separation and determination of the optical purity of thiamphenicol-related chiral compound by capillary zone electrophoresis with cyclodextrins as chiral selectors [J].
Kang, JW ;
Zhang, XM ;
Zhang, SM ;
Ou, QY .
CHROMATOGRAPHIA, 1999, 50 (5-6) :317-320
[47]   Chiral separation and determination of the optical purity of thiamphenicol-related chiral compound by capillary zone electrophoresis with cyclodextrins as chiral selectors [J].
Jing-Wu Kang ;
Xiao-Mei Zhang ;
Suo-Ming Zhang ;
Qing-Yu Ou .
Chromatographia, 1999, 50 :317-320
[48]   Chiral Separation of Oxazolidinone Analogs by Capillary Electrophoresis Using Anionic Cyclodextrins as Chiral Selectors: Emphasis on Enantiomer Migration Order [J].
Szabo, Zoltan-Istvan ;
Boda, Francisc ;
Fiser, Bela ;
Dobo, Mate ;
Szocs, Levente ;
Toth, Gergo .
MOLECULES, 2023, 28 (11)
[49]   Dependence of chiral separations on the amount of cyclodextrins as selectors, employing the partial filling technique in capillary zone electrophoresis [J].
A. Amini ;
U. Paulsen-Sörman ;
D. Westerlund .
Chromatographia, 2000, 51 :226-230
[50]   Dependence of chiral separations on the amount of cyclodextrins as selectors, employing the partial filling technique in capillary zone electrophoresis [J].
Amini, A ;
Paulsen-Sörman, U ;
Westerlund, D .
CHROMATOGRAPHIA, 2000, 51 (3-4) :226-230