LC enantioseparation of β-lactam and β-amino acid stereoisomers and a comparison of macrocyclic glycopeptide- and β-cyclodextrin-based columns

R. Berkecz, R. Török, I. Ilisz, E. Forró, F. Fülöp, D. W. Armstrong, A. Péter

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29 Citations (Scopus)

Abstract

Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of the enantiomers of tricyclic β-lactams, cis-3,4-benzo-6-azabicyclo[3.2.0]heptan-7-one, cis-4,5-benzo-7-azabicyclo[4.2.0] -octan-8-one, cis-5,6-benzo-8-azabicyclo[5.2.0]nonan-9-one and new bicyclic β-amino acids, the six- and seven-membered homologues of cis-1-amino-4,5-benzocyclopentane-2-carboxylic acid (benzocispentacin), cis-1-amino-5,6-benzocyclohexane-2-carboxylic acid and cis-1-amino-6,7- benzocycloheptane-2-carboxylic acid. The direct separations of the analytes were performed on chiral stationary phase (CSP) columns containing the macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T), teicoplanin aglycone (Chirobiotic TAG), vancomycin (Chirobiotic V), vancomycin aglycone (Chirobiotic VAG), ristocetin A (Chirobiotic R) or a new dimethylphenyl carbamate-derivatized β-cyclodextrin-based Cyclobond DMP. The results achieved with the different methods were compared in systematic chromatographic examinations. The effects of an organic modifier and of the mobile phase composition on the separation and the separation efficiency of different columns were investigated. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP for these β-lactams and β-amino acids ranged between 0.3 and -1.1 kJmol-1. Better enantioseparations were attained in most cases on the aglycone CSP.

Original languageEnglish
JournalChromatographia
Volume63
Issue numberSUPPL. 13
DOIs
Publication statusPublished - Jun 2006

Fingerprint

Lactams
Stereoisomerism
Glycopeptides
Cyclodextrins
Carboxylic Acids
Teicoplanin
Vancomycin
Amino Acids
Carbamates
Enantiomers
Phase composition
Free energy
Anti-Bacterial Agents
Liquids

Keywords

  • β-Amino acids
  • β-Lactams
  • Chirobiotic T and TAG columns
  • Column liquid chromatography
  • Cyclobond DMP column

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

@article{130805a5e0e648c1a64f93c1d719e672,
title = "LC enantioseparation of β-lactam and β-amino acid stereoisomers and a comparison of macrocyclic glycopeptide- and β-cyclodextrin-based columns",
abstract = "Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of the enantiomers of tricyclic β-lactams, cis-3,4-benzo-6-azabicyclo[3.2.0]heptan-7-one, cis-4,5-benzo-7-azabicyclo[4.2.0] -octan-8-one, cis-5,6-benzo-8-azabicyclo[5.2.0]nonan-9-one and new bicyclic β-amino acids, the six- and seven-membered homologues of cis-1-amino-4,5-benzocyclopentane-2-carboxylic acid (benzocispentacin), cis-1-amino-5,6-benzocyclohexane-2-carboxylic acid and cis-1-amino-6,7- benzocycloheptane-2-carboxylic acid. The direct separations of the analytes were performed on chiral stationary phase (CSP) columns containing the macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T), teicoplanin aglycone (Chirobiotic TAG), vancomycin (Chirobiotic V), vancomycin aglycone (Chirobiotic VAG), ristocetin A (Chirobiotic R) or a new dimethylphenyl carbamate-derivatized β-cyclodextrin-based Cyclobond DMP. The results achieved with the different methods were compared in systematic chromatographic examinations. The effects of an organic modifier and of the mobile phase composition on the separation and the separation efficiency of different columns were investigated. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP for these β-lactams and β-amino acids ranged between 0.3 and -1.1 kJmol-1. Better enantioseparations were attained in most cases on the aglycone CSP.",
keywords = "β-Amino acids, β-Lactams, Chirobiotic T and TAG columns, Column liquid chromatography, Cyclobond DMP column",
author = "R. Berkecz and R. T{\"o}r{\"o}k and I. Ilisz and E. Forr{\'o} and F. F{\"u}l{\"o}p and Armstrong, {D. W.} and A. P{\'e}ter",
year = "2006",
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T1 - LC enantioseparation of β-lactam and β-amino acid stereoisomers and a comparison of macrocyclic glycopeptide- and β-cyclodextrin-based columns

AU - Berkecz, R.

AU - Török, R.

AU - Ilisz, I.

AU - Forró, E.

AU - Fülöp, F.

AU - Armstrong, D. W.

AU - Péter, A.

PY - 2006/6

Y1 - 2006/6

N2 - Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of the enantiomers of tricyclic β-lactams, cis-3,4-benzo-6-azabicyclo[3.2.0]heptan-7-one, cis-4,5-benzo-7-azabicyclo[4.2.0] -octan-8-one, cis-5,6-benzo-8-azabicyclo[5.2.0]nonan-9-one and new bicyclic β-amino acids, the six- and seven-membered homologues of cis-1-amino-4,5-benzocyclopentane-2-carboxylic acid (benzocispentacin), cis-1-amino-5,6-benzocyclohexane-2-carboxylic acid and cis-1-amino-6,7- benzocycloheptane-2-carboxylic acid. The direct separations of the analytes were performed on chiral stationary phase (CSP) columns containing the macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T), teicoplanin aglycone (Chirobiotic TAG), vancomycin (Chirobiotic V), vancomycin aglycone (Chirobiotic VAG), ristocetin A (Chirobiotic R) or a new dimethylphenyl carbamate-derivatized β-cyclodextrin-based Cyclobond DMP. The results achieved with the different methods were compared in systematic chromatographic examinations. The effects of an organic modifier and of the mobile phase composition on the separation and the separation efficiency of different columns were investigated. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP for these β-lactams and β-amino acids ranged between 0.3 and -1.1 kJmol-1. Better enantioseparations were attained in most cases on the aglycone CSP.

AB - Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of the enantiomers of tricyclic β-lactams, cis-3,4-benzo-6-azabicyclo[3.2.0]heptan-7-one, cis-4,5-benzo-7-azabicyclo[4.2.0] -octan-8-one, cis-5,6-benzo-8-azabicyclo[5.2.0]nonan-9-one and new bicyclic β-amino acids, the six- and seven-membered homologues of cis-1-amino-4,5-benzocyclopentane-2-carboxylic acid (benzocispentacin), cis-1-amino-5,6-benzocyclohexane-2-carboxylic acid and cis-1-amino-6,7- benzocycloheptane-2-carboxylic acid. The direct separations of the analytes were performed on chiral stationary phase (CSP) columns containing the macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T), teicoplanin aglycone (Chirobiotic TAG), vancomycin (Chirobiotic V), vancomycin aglycone (Chirobiotic VAG), ristocetin A (Chirobiotic R) or a new dimethylphenyl carbamate-derivatized β-cyclodextrin-based Cyclobond DMP. The results achieved with the different methods were compared in systematic chromatographic examinations. The effects of an organic modifier and of the mobile phase composition on the separation and the separation efficiency of different columns were investigated. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP for these β-lactams and β-amino acids ranged between 0.3 and -1.1 kJmol-1. Better enantioseparations were attained in most cases on the aglycone CSP.

KW - β-Amino acids

KW - β-Lactams

KW - Chirobiotic T and TAG columns

KW - Column liquid chromatography

KW - Cyclobond DMP column

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U2 - 10.1365/s10337-005-0701-x

DO - 10.1365/s10337-005-0701-x

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