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

doi:10.1002/jssc.200900732

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^*

^*Corresponding author for this work

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

37 Citations (Scopus)

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 language	English
Pages (from-to)	1797-1805
Number of pages	9
Journal	Journal of Separation Science
Volume	33
Issue number	12
DOIs	https://doi.org/10.1002/jssc.200900732
Publication status	Published - Jun 2010
Externally published	Yes

ASJC Scopus Subject Areas

Analytical Chemistry
Filtration and Separation

Keywords

Capillary electrophoresis
Enantioseparation
Positively charged β-cyclodextrin

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10.1002/jssc.200900732

Cite this

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title = "Chiral capillary electrophoresis with cationic pyrrolidinium-β- cyclodextrin derivatives as chiral selectors",

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}",

year = "2010",

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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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N2 - 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.

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

Abstract

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Keywords

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