Characterization of a Thermally Induced Irreversible Conformational Transition of Amylose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phase in Enantioseparation of Dihydropyrimidinone Acid by Quasi-Equilibrated Liquid Chromatography and Solid-State NMR

Fang Wang, Robert M. Wenslow, Thomas M. Dowling, Karl Todd Mueller, Ivan Santos, Jean M. Wyvratt

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

A thermally induced irreversible conformational transition of amylose tris(3,5-dimethylphenylcarbamate) (i.e., Chiralpak AD) chiral stationary phase (CSP) in the enantioseparation of dihydropyrimidinone (DHP) acid racemate was studied for the first time by quasi-equilibrated liquid chromatography with cyclic van't Hoff and step temperature programs and solid-state (13C CPMAS and 19F MAS) NMR using ethanol and trifluoroacetic acid (TFA)-modified n-hexane as the mobile phase. The conformational transition was controlled by a single kinetically driven process, as evidenced by the chromatographic studies. Solid-state NMR was used to study the effect of the temperature on the conformational change of the solvated phase (with or without the DHP acid enantiomers and TFA) and provided some viable structural information about the CSP and the enantiomers.

Original languageEnglish (US)
Pages (from-to)5877-5885
Number of pages9
JournalAnalytical Chemistry
Volume75
Issue number21
DOIs
StatePublished - Nov 1 2003

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Trifluoroacetic Acid
Enantiomers
Liquid chromatography
Nuclear magnetic resonance
Acids
Ethanol
Temperature
Chiralpak AD
n-hexane

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry

Cite this

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title = "Characterization of a Thermally Induced Irreversible Conformational Transition of Amylose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phase in Enantioseparation of Dihydropyrimidinone Acid by Quasi-Equilibrated Liquid Chromatography and Solid-State NMR",
abstract = "A thermally induced irreversible conformational transition of amylose tris(3,5-dimethylphenylcarbamate) (i.e., Chiralpak AD) chiral stationary phase (CSP) in the enantioseparation of dihydropyrimidinone (DHP) acid racemate was studied for the first time by quasi-equilibrated liquid chromatography with cyclic van't Hoff and step temperature programs and solid-state (13C CPMAS and 19F MAS) NMR using ethanol and trifluoroacetic acid (TFA)-modified n-hexane as the mobile phase. The conformational transition was controlled by a single kinetically driven process, as evidenced by the chromatographic studies. Solid-state NMR was used to study the effect of the temperature on the conformational change of the solvated phase (with or without the DHP acid enantiomers and TFA) and provided some viable structural information about the CSP and the enantiomers.",
author = "Fang Wang and Wenslow, {Robert M.} and Dowling, {Thomas M.} and Mueller, {Karl Todd} and Ivan Santos and Wyvratt, {Jean M.}",
year = "2003",
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language = "English (US)",
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journal = "Analytical Chemistry",
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Characterization of a Thermally Induced Irreversible Conformational Transition of Amylose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phase in Enantioseparation of Dihydropyrimidinone Acid by Quasi-Equilibrated Liquid Chromatography and Solid-State NMR. / Wang, Fang; Wenslow, Robert M.; Dowling, Thomas M.; Mueller, Karl Todd; Santos, Ivan; Wyvratt, Jean M.

In: Analytical Chemistry, Vol. 75, No. 21, 01.11.2003, p. 5877-5885.

Research output: Contribution to journalArticle

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AU - Wang, Fang

AU - Wenslow, Robert M.

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AU - Mueller, Karl Todd

AU - Santos, Ivan

AU - Wyvratt, Jean M.

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