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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