Evaluation of chiral discrimination of highly negatively charged enantiomers by quaternary ammonium β‐cyclodextrin using 1H NMR

Qinfeng Liu; L. M. Viranga Tellekeratne; Y. Kim; J. R. Kirchhoff; R. A. Hudson

doi:10.1002/chir.20209

Evaluation of chiral discrimination of highly negatively charged enantiomers by quaternary ammonium β‐cyclodextrin using 1H NMR

Qinfeng Liu
, L. M. Viranga Tellekeratne
, Y. Kim
, J. R. Kirchhoff
, R. A. Hudson

Campbell University

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

Abstract

The positively charged quaternary ammonium cyclodextrin, QA&hyphen;β&hyphen;CD, was previously used as a chiral selector to achieve baseline resolution of two of the dianionic enantiomers of disodium 3&hyphen;( p &hyphen;isothiocyanatophenoxy)&hyphen;3&hyphen;( p &hyphen;isothiocyanatophenyl)propane&hyphen;1,2&hyphen;disulfate by capillary electrophoresis. The basis of the chiral discrimination between QA&hyphen;β&hyphen;CD and the enantiomers was investigated by 1H NMR spectroscopy. COSY and NOESY spectra were used to infer the role that molecular interactions and the stereocenters have upon association of QA&hyphen;β&hyphen;CD with the enantiomers. A parallel two&hyphen;step complexation model is used to rationalize the NMR and the chiral discrimination observed during separation of the enantiomers. © 2005 Wiley&hyphen;Liss, Inc. Chirality 17:570–576, 2005.

Original language	American English
Journal	Chirality
Volume	17
DOIs	https://doi.org/10.1002/chir.20209
State	Published - Oct 7 2005

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Pharmacy and Pharmaceutical Sciences

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@article{2162d2cc3c924555b743dfd25a2c798c,

title = "Evaluation of chiral discrimination of highly negatively charged enantiomers by quaternary ammonium β‐cyclodextrin using 1H NMR",

abstract = " The positively charged quaternary ammonium cyclodextrin, QA\&hyphen;\β\&hyphen;CD, was previously used as a chiral selector to achieve baseline resolution of two of the dianionic enantiomers of disodium 3\&hyphen;( p \&hyphen;isothiocyanatophenoxy)\&hyphen;3\&hyphen;( p \&hyphen;isothiocyanatophenyl)propane\&hyphen;1,2\&hyphen;disulfate by capillary electrophoresis. The basis of the chiral discrimination between QA\&hyphen;\β\&hyphen;CD and the enantiomers was investigated by 1H NMR spectroscopy. COSY and NOESY spectra were used to infer the role that molecular interactions and the stereocenters have upon association of QA\&hyphen;\β\&hyphen;CD with the enantiomers. A parallel two\&hyphen;step complexation model is used to rationalize the NMR and the chiral discrimination observed during separation of the enantiomers. \© 2005 Wiley\&hyphen;Liss, Inc. Chirality 17:570\–576, 2005. ",

author = "Qinfeng Liu and \{Viranga Tellekeratne\}, \{L. M.\} and Y. Kim and Kirchhoff, \{J. R.\} and Hudson, \{R. A.\}",

year = "2005",

month = oct,

day = "7",

doi = "10.1002/chir.20209",

language = "American English",

volume = "17",

journal = "Chirality",

}

TY - JOUR

T1 - Evaluation of chiral discrimination of highly negatively charged enantiomers by quaternary ammonium β‐cyclodextrin using 1H NMR

AU - Liu, Qinfeng

AU - Viranga Tellekeratne, L. M.

AU - Kim, Y.

AU - Kirchhoff, J. R.

AU - Hudson, R. A.

PY - 2005/10/7

Y1 - 2005/10/7

N2 - The positively charged quaternary ammonium cyclodextrin, QA&hyphen;β&hyphen;CD, was previously used as a chiral selector to achieve baseline resolution of two of the dianionic enantiomers of disodium 3&hyphen;( p &hyphen;isothiocyanatophenoxy)&hyphen;3&hyphen;( p &hyphen;isothiocyanatophenyl)propane&hyphen;1,2&hyphen;disulfate by capillary electrophoresis. The basis of the chiral discrimination between QA&hyphen;β&hyphen;CD and the enantiomers was investigated by 1H NMR spectroscopy. COSY and NOESY spectra were used to infer the role that molecular interactions and the stereocenters have upon association of QA&hyphen;β&hyphen;CD with the enantiomers. A parallel two&hyphen;step complexation model is used to rationalize the NMR and the chiral discrimination observed during separation of the enantiomers. © 2005 Wiley&hyphen;Liss, Inc. Chirality 17:570–576, 2005.

AB - The positively charged quaternary ammonium cyclodextrin, QA&hyphen;β&hyphen;CD, was previously used as a chiral selector to achieve baseline resolution of two of the dianionic enantiomers of disodium 3&hyphen;( p &hyphen;isothiocyanatophenoxy)&hyphen;3&hyphen;( p &hyphen;isothiocyanatophenyl)propane&hyphen;1,2&hyphen;disulfate by capillary electrophoresis. The basis of the chiral discrimination between QA&hyphen;β&hyphen;CD and the enantiomers was investigated by 1H NMR spectroscopy. COSY and NOESY spectra were used to infer the role that molecular interactions and the stereocenters have upon association of QA&hyphen;β&hyphen;CD with the enantiomers. A parallel two&hyphen;step complexation model is used to rationalize the NMR and the chiral discrimination observed during separation of the enantiomers. © 2005 Wiley&hyphen;Liss, Inc. Chirality 17:570–576, 2005.

UR - https://cufind.campbell.edu/pharmacy/1967

UR - https://doi.org/10.1002/chir.20209

U2 - 10.1002/chir.20209

DO - 10.1002/chir.20209

M3 - Article

VL - 17

JO - Chirality

JF - Chirality

ER -

Evaluation of chiral discrimination of highly negatively charged enantiomers by quaternary ammonium β‐cyclodextrin using 1H NMR

Abstract

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