Chiral capillary electrophoresis with cationic pyrrolidinium-β- cyclodextrin derivatives as chiral selectors

Yin Xiao, Yong Wang, Teng Teng Ong, Liya Ge, Swee Ngin Tan, David J. Young, T. T.Y. Tan, Siu Choon Ng

Research output: Contribution to journalArticleResearchpeer-review

Abstract

New single-isomer, cationic β-cyclodextrins, including mono-6-deoxy-6-pyrrolidine-β-cyclodextrin chloride (pyCDCl), mono-6-deoxy-6-(N-methyl-pyrrolidine)-β-cyclodextrin chloride (N-CH 3-pyCDCl), mono-6-deoxy-6-(N-(2-hydroxyethyl)-pyrrolidine)-β- cyclodextrin chloride (NEtOH-pyCDCl), mono-6-deoxy-6-(2-hydroxymethyl- pyrrolidine)-β-cyclodextrin chloride (2-MeOH-pyCDCl) were synthesized and used as chiral selectors in capillary electrophoresis for the enantioseparation of carboxylic and hydroxycarboxylic acids and dansyl amino acids. The unsubstituted pyCDCl exhibited the greatest resolving ability. Most analytes were resolved over a wide range of pH from 6.0 to 9.0 with this chiral selector. In general, increasing pH led to a decrease in resolution. The effective mobilities of all the analytes were found to decrease with increasing CD concentration. The optimal concentration for most carboxylic acids and dansyl amino acid was in the range 5-7.5mM and >15mM for hydroxycarboxylic acids. 1H NMR experiments provided direct evidence of inclusion in the CD cavity.

Original languageEnglish
Pages (from-to)1797-1805
Number of pages9
JournalJournal of Separation Science
Volume33
Issue number12
DOIs
Publication statusPublished - Jun 2010
Externally publishedYes

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Capillary electrophoresis
Cyclodextrins
Chlorides
Derivatives
Amino acids
Amino Acids
Acids
Carboxylic Acids
pyrrolidine
Carboxylic acids
Isomers
Nuclear magnetic resonance

Cite this

Xiao, Yin ; Wang, Yong ; Ong, Teng Teng ; Ge, Liya ; Tan, Swee Ngin ; Young, David J. ; Tan, T. T.Y. ; Ng, Siu Choon. / Chiral capillary electrophoresis with cationic pyrrolidinium-β- cyclodextrin derivatives as chiral selectors. In: Journal of Separation Science. 2010 ; Vol. 33, No. 12. pp. 1797-1805.
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abstract = "New single-isomer, cationic β-cyclodextrins, including mono-6-deoxy-6-pyrrolidine-β-cyclodextrin chloride (pyCDCl), mono-6-deoxy-6-(N-methyl-pyrrolidine)-β-cyclodextrin chloride (N-CH 3-pyCDCl), mono-6-deoxy-6-(N-(2-hydroxyethyl)-pyrrolidine)-β- cyclodextrin chloride (NEtOH-pyCDCl), mono-6-deoxy-6-(2-hydroxymethyl- pyrrolidine)-β-cyclodextrin chloride (2-MeOH-pyCDCl) were synthesized and used as chiral selectors in capillary electrophoresis for the enantioseparation of carboxylic and hydroxycarboxylic acids and dansyl amino acids. The unsubstituted pyCDCl exhibited the greatest resolving ability. Most analytes were resolved over a wide range of pH from 6.0 to 9.0 with this chiral selector. In general, increasing pH led to a decrease in resolution. The effective mobilities of all the analytes were found to decrease with increasing CD concentration. The optimal concentration for most carboxylic acids and dansyl amino acid was in the range 5-7.5mM and >15mM for hydroxycarboxylic acids. 1H NMR experiments provided direct evidence of inclusion in the CD cavity.",
keywords = "Capillary electrophoresis, Enantioseparation, Positively charged β-cyclodextrin",
author = "Yin Xiao and Yong Wang and Ong, {Teng Teng} and Liya Ge and Tan, {Swee Ngin} and Young, {David J.} and Tan, {T. T.Y.} and Ng, {Siu Choon}",
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Chiral capillary electrophoresis with cationic pyrrolidinium-β- cyclodextrin derivatives as chiral selectors. / Xiao, Yin; Wang, Yong; Ong, Teng Teng; Ge, Liya; Tan, Swee Ngin; Young, David J.; Tan, T. T.Y.; Ng, Siu Choon.

In: Journal of Separation Science, Vol. 33, No. 12, 06.2010, p. 1797-1805.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Chiral capillary electrophoresis with cationic pyrrolidinium-β- cyclodextrin derivatives as chiral selectors

AU - Xiao, Yin

AU - Wang, Yong

AU - Ong, Teng Teng

AU - Ge, Liya

AU - Tan, Swee Ngin

AU - Young, David J.

AU - Tan, T. T.Y.

AU - Ng, Siu Choon

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AB - New single-isomer, cationic β-cyclodextrins, including mono-6-deoxy-6-pyrrolidine-β-cyclodextrin chloride (pyCDCl), mono-6-deoxy-6-(N-methyl-pyrrolidine)-β-cyclodextrin chloride (N-CH 3-pyCDCl), mono-6-deoxy-6-(N-(2-hydroxyethyl)-pyrrolidine)-β- cyclodextrin chloride (NEtOH-pyCDCl), mono-6-deoxy-6-(2-hydroxymethyl- pyrrolidine)-β-cyclodextrin chloride (2-MeOH-pyCDCl) were synthesized and used as chiral selectors in capillary electrophoresis for the enantioseparation of carboxylic and hydroxycarboxylic acids and dansyl amino acids. The unsubstituted pyCDCl exhibited the greatest resolving ability. Most analytes were resolved over a wide range of pH from 6.0 to 9.0 with this chiral selector. In general, increasing pH led to a decrease in resolution. The effective mobilities of all the analytes were found to decrease with increasing CD concentration. The optimal concentration for most carboxylic acids and dansyl amino acid was in the range 5-7.5mM and >15mM for hydroxycarboxylic acids. 1H NMR experiments provided direct evidence of inclusion in the CD cavity.

KW - Capillary electrophoresis

KW - Enantioseparation

KW - Positively charged β-cyclodextrin

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