Analysis of the band profiles of the enantiomers of phenylglycine in liquid chromatography on bonded teicoplanin columns using the stochastic theory of chromatography

Pavel Jandera, Veronika Bačkovská, A. Felinger

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Abstract

The retention behaviour of the enantiomers of underivatized phenylglycine was studied on a Chirobiotic T column packed with amphoteric glycopeptide teicoplanin covalently bonded to the surface of silica gel. The retention and the selectivity of separation of the enantiomers increase with rising concentration of ethanol or of methanol in aqueous-organic mobile phases. The band profiles of the less retained L-phenylglycine are symmetrical, but the band profiles of the more strongly retained D-phenylglycine are tailing in all mobile phases tested. The band broadening does not diminish even at very low concentrations of phenylglycine, so that it cannot be attributed to possible column overload. The analysis of the band profile using the stochastic theory of chromatography suggests that the broadening can be attributed to at least two additional chiral centres of adsorption in the stationary phase contributing to the retention of the more strongly retained enantiomer in addition to the adsorption of the less retained one. This behaviour can be explained by the complex structure of the teicoplanin chiral stationary phase.

Original languageEnglish
Pages (from-to)67-77
Number of pages11
JournalJournal of Chromatography A
Volume919
Issue number1
DOIs
Publication statusPublished - Jun 1 2001

Fingerprint

Teicoplanin
Enantiomers
Liquid chromatography
Chromatography
Liquid Chromatography
Adsorption
Glycopeptides
Silica Gel
Methanol
Ethanol
Tailings
2-phenylglycine
chirobiotic T

Keywords

  • Band profiles
  • Chiral stationary phases, LC
  • Enantiomer separation
  • Phenylglycine
  • Stochastic theory
  • Teicoplanin

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

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title = "Analysis of the band profiles of the enantiomers of phenylglycine in liquid chromatography on bonded teicoplanin columns using the stochastic theory of chromatography",
abstract = "The retention behaviour of the enantiomers of underivatized phenylglycine was studied on a Chirobiotic T column packed with amphoteric glycopeptide teicoplanin covalently bonded to the surface of silica gel. The retention and the selectivity of separation of the enantiomers increase with rising concentration of ethanol or of methanol in aqueous-organic mobile phases. The band profiles of the less retained L-phenylglycine are symmetrical, but the band profiles of the more strongly retained D-phenylglycine are tailing in all mobile phases tested. The band broadening does not diminish even at very low concentrations of phenylglycine, so that it cannot be attributed to possible column overload. The analysis of the band profile using the stochastic theory of chromatography suggests that the broadening can be attributed to at least two additional chiral centres of adsorption in the stationary phase contributing to the retention of the more strongly retained enantiomer in addition to the adsorption of the less retained one. This behaviour can be explained by the complex structure of the teicoplanin chiral stationary phase.",
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AU - Bačkovská, Veronika

AU - Felinger, A.

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N2 - The retention behaviour of the enantiomers of underivatized phenylglycine was studied on a Chirobiotic T column packed with amphoteric glycopeptide teicoplanin covalently bonded to the surface of silica gel. The retention and the selectivity of separation of the enantiomers increase with rising concentration of ethanol or of methanol in aqueous-organic mobile phases. The band profiles of the less retained L-phenylglycine are symmetrical, but the band profiles of the more strongly retained D-phenylglycine are tailing in all mobile phases tested. The band broadening does not diminish even at very low concentrations of phenylglycine, so that it cannot be attributed to possible column overload. The analysis of the band profile using the stochastic theory of chromatography suggests that the broadening can be attributed to at least two additional chiral centres of adsorption in the stationary phase contributing to the retention of the more strongly retained enantiomer in addition to the adsorption of the less retained one. This behaviour can be explained by the complex structure of the teicoplanin chiral stationary phase.

AB - The retention behaviour of the enantiomers of underivatized phenylglycine was studied on a Chirobiotic T column packed with amphoteric glycopeptide teicoplanin covalently bonded to the surface of silica gel. The retention and the selectivity of separation of the enantiomers increase with rising concentration of ethanol or of methanol in aqueous-organic mobile phases. The band profiles of the less retained L-phenylglycine are symmetrical, but the band profiles of the more strongly retained D-phenylglycine are tailing in all mobile phases tested. The band broadening does not diminish even at very low concentrations of phenylglycine, so that it cannot be attributed to possible column overload. The analysis of the band profile using the stochastic theory of chromatography suggests that the broadening can be attributed to at least two additional chiral centres of adsorption in the stationary phase contributing to the retention of the more strongly retained enantiomer in addition to the adsorption of the less retained one. This behaviour can be explained by the complex structure of the teicoplanin chiral stationary phase.

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