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

Dolors Salvatierra; Xavier Sánchez-Ruiz; Ramón Garduño; Enric Cervelló; Carlos Jaime; Albert Virgili; Francisco Sánchez-Ferrando

doi:10.1016/S0040-4020(00)00192-7

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

Dolors Salvatierra, Xavier Sánchez-Ruiz, Ramón Garduño, Enric Cervelló, Carlos Jaime, Albert Virgili, Francisco Sánchez-Ferrando

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

31 Citations (Scopus)

Abstract

Diastereomeric complexes between [β-CyD and both enantiomers of mandelic acid, hexahydromandelic acid, and 1-cyclohexylethylamine were studied by NMR spectroscopy. Their inclusion complexes were studied by molecular dynamics (MD) calculations. Induced chemical shifts gave association constants of about 102-103 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 diastereomer when enantiomers are individually complexed with β- CyD. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	3035-3041
Journal	Tetrahedron
Volume	56
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4020(00)00192-7
Publication status	Published - 5 May 2000

Keywords

Complexes
Cyclodextrins
Molecular modeling
Molecular recognition

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title = "Enantiodifferentiation by complexation with β-cyclodextrin: Experimental (NMR) and theoretical (MD, FEP) studies",

abstract = "Diastereomeric complexes between [β-CyD and both enantiomers of mandelic acid, hexahydromandelic acid, and 1-cyclohexylethylamine were studied by NMR spectroscopy. Their inclusion complexes were studied by molecular dynamics (MD) calculations. Induced chemical shifts gave association constants of about 102-103 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 diastereomer when enantiomers are individually complexed with β- CyD. (C) 2000 Elsevier Science Ltd.",

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Enantiodifferentiation by complexation with β-cyclodextrin: Experimental (NMR) and theoretical (MD, FEP) studies. / Salvatierra, Dolors; Sánchez-Ruiz, Xavier; Garduño, Ramón; Cervelló, Enric; Jaime, Carlos ; Virgili, Albert; Sánchez-Ferrando, Francisco.

In: Tetrahedron, Vol. 56, No. 19, 05.05.2000, p. 3035-3041.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Enantiodifferentiation by complexation with β-cyclodextrin: Experimental (NMR) and theoretical (MD, FEP) studies

AU - Salvatierra, Dolors

AU - Sánchez-Ruiz, Xavier

AU - Garduño, Ramón

AU - Cervelló, Enric

AU - Jaime, Carlos

AU - Virgili, Albert

AU - Sánchez-Ferrando, Francisco

PY - 2000/5/5

Y1 - 2000/5/5

N2 - Diastereomeric complexes between [β-CyD and both enantiomers of mandelic acid, hexahydromandelic acid, and 1-cyclohexylethylamine were studied by NMR spectroscopy. Their inclusion complexes were studied by molecular dynamics (MD) calculations. Induced chemical shifts gave association constants of about 102-103 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 diastereomer when enantiomers are individually complexed with β- CyD. (C) 2000 Elsevier Science Ltd.

AB - Diastereomeric complexes between [β-CyD and both enantiomers of mandelic acid, hexahydromandelic acid, and 1-cyclohexylethylamine were studied by NMR spectroscopy. Their inclusion complexes were studied by molecular dynamics (MD) calculations. Induced chemical shifts gave association constants of about 102-103 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 diastereomer when enantiomers are individually complexed with β- CyD. (C) 2000 Elsevier Science Ltd.

KW - Complexes

KW - Cyclodextrins

KW - Molecular modeling

KW - Molecular recognition

U2 - 10.1016/S0040-4020(00)00192-7

DO - 10.1016/S0040-4020(00)00192-7

M3 - Article

VL - 56

SP - 3035

EP - 3041

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 19

ER -