Enantiodifferentiation by complexation with beta-cyclodextrin: Experimental (NMR) and theoretical (MD, FEP) studies

Authors
Salvatierra, D Sanchez-Ruiz, X Garduno, R Cervello, E Jaime, C Virgili, A Sanchez-Ferrando, F
Citation
D. Salvatierra et al., Enantiodifferentiation by complexation with beta-cyclodextrin: Experimental (NMR) and theoretical (MD, FEP) studies, TETRAHEDRON, 56(19), 2000, pp. 3035-3041
Citations number
72
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
19
Year of publication
2000
Pages
3035 - 3041
Database
ISI
SICI code
0040-4020(20000505)56:19<3035:EBCWBE>2.0.ZU;2-P
Abstract
Diastereomeric complexes between beta-CyD and both enantiomers of mandelic acid, hexahydromandelic acid, and 1-cyclohexylethylamine were studied by NM R spectroscopy. Their inclusion complexes were studied by molecular dynamic s (MD) calculations. Induced chemical shifts gave association constants of about 10(2)-10(3) M-1. Computed geometries for the inclusion complexes are in agreement with those deduced experimentally by NOE experiments. MD (free energy perturbation) calculations correctly predict the most stable diaste reomer when enantiomers are individually complexed with beta-CyD. (C) 2000 Elsevier Science Ltd. All rights reserved.