Applications of nuclear magnetic resonance spectroscopy for the understanding of enantiomer separation mechanisms in capillary electrophoresis.

作者: Antonio Salgado , Bezhan Chankvetadze

DOI: 10.1016/J.CHROMA.2016.08.060

关键词:

摘要: Abstract This review deals with the applications of nuclear magnetic resonance (NMR) spectroscopy to understand mechanisms chiral separation in capillary electrophoresis (CE). It is accepted that changes observed process, including reversal enantiomer migration order (EMO), can be caused by subtle modifications molecular recognition between and selector. These may imply minor structural differences those selector-selectand complexes arise from above mentioned interactions. Therefore, it mandatory fine intermolecular interactions analytes selectors. In other words, necessary know detail structures formed (selectand) Any these arising either should detected, so enantiomeric bias process could explained. As nature interactions, have been extensively reviewed, not intended discussed here. contemplate ionic, ion-dipole dipole–dipole hydrogen bonding, van der Waals forces, π − π stacking, steric hydrophobic The main subject this describe how NMR helps gain insight into non-covalent selector selectand lead CE. Examples which diastereomeric species are created covalent (irreversible) derivatization will considered structured upon different classes selectors employed CE, has made substantial contributions rationalize enantioseparations. Cases techniques complement spectroscopic data also mentioned.

参考文章(120)
S.K. Branch, U. Holzgrabe, T.M. Jefferies, H. Mallwitz, M.W. Matchett, Chiral discrimination of phenethylamines with β-cyclodextrin and heptakis(2,3-di-O-acetyl)β-cyclodextrin by capillary electrophoresis and NMR spectroscopy Journal of Pharmaceutical and Biomedical Analysis. ,vol. 12, pp. 1507- 1517 ,(1994) , 10.1016/0731-7085(94)00080-8
Joseph K. Rugutt, H. Hyacinthe Yarabe, Shahab A. Shamsi, Damon R. Billodeaux, Frank R. Fronczek, Isiah M. Warner, GR 24 enantiomers: synthesis, NMR spectroscopy, X-ray crystallography, and separation by chiral electrokinetic capillary chromatography. Analytical Chemistry. ,vol. 72, pp. 3887- 3895 ,(2000) , 10.1021/AC991438O
Bezhan Chankvetadze, Gabriele Endresz, Dieter Bergenthal, Gottfried Blaschke, Enantioseparation of mianserine analogues using capillary electrophoresis with neutral and charged cyclodextrin buffer modifiers 13C NMR study of the chiral recognition mechanism Journal of Chromatography A. ,vol. 717, pp. 245- 253 ,(1995) , 10.1016/0021-9673(95)00489-4
Jie Zhou, Yiying Wang, Yun Liu, Jian Tang, Weihua Tang, Methoxypropylamino β-cyclodextrin clicked AC regioisomer for enantioseparations in capillary electrophoresis Analytica Chimica Acta. ,vol. 868, pp. 73- 79 ,(2015) , 10.1016/J.ACA.2015.02.013
Bezhan Chankvetadze, Naira Burjanadze, Giorgio Pintore, Dieter Bergenthal, Klaus Bergander, Christoph Mühlenbrock, Jörg Breitkreuz, Gottfried Blaschke, Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV spectrometry, electrospray ionization mass spectrometry and X-ray crystallography. Journal of Chromatography A. ,vol. 875, pp. 471- 484 ,(2000) , 10.1016/S0021-9673(00)00153-9
Robert L. Scott, Some comments on the Benesi-Hildebrand equation Recueil des Travaux Chimiques des Pays-Bas. ,vol. 75, pp. 787- 789 ,(2010) , 10.1002/RECL.19560750711
Mikhail V. Rekharsky, Robert N. Goldberg, Frederick P. Schwarz, Yadu B. Tewari, Philip D. Ross, Yuko Yamashoji, Yoshihisa Inoue, Thermodynamic and Nuclear Magnetic Resonance Study of the Interactions of .alpha.- and .beta.-Cyclodextrin with Model Substances: Phenethylamine, Ephedrines, and Related Substances Journal of the American Chemical Society. ,vol. 117, pp. 8830- 8840 ,(1995) , 10.1021/JA00139A017
Katleen Verleysen, Pat Sandra, Separation of chiral compounds by capillary electrophoresis. Electrophoresis. ,vol. 19, pp. 2798- 2833 ,(1998) , 10.1002/ELPS.1150191607