Comparison of separation performances of amylose- and cellulose-based stationary phases in the high-performance liquid chromatographic enantioseparation of stereoisomers of β-lactams

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Abstract

High-performance liquid chromatographic methods were developed for the separation of the enantiomers of 19 β-lactams. The direct separations were performed on chiral stationary phases containing either amylose-tris-3,5- dimethylphenyl carbamate, (Kromasil® AmyCoat™ column) or cellulose-tris-3,5-dimethylphenyl carbamate, (Kromasil® CelluCoat™ column) as chiral selector. The different methods were compared in systematic chromatographic examinations. The separations were carried out with good selectivity and resolution. The AmyCoat™ and CelluCoat™ columns appear to be highly complementary. The best separations of bi- and tricyclic b-lactam stereoisomers were obtained with the AmyCoat™ column, whereas the 4-aryl-substituted β-lactams were better separated on the CelluCoat™ column. The elution sequence was determined in all cases; no general rule could be established.

Original languageEnglish
Pages (from-to)120-128
Number of pages9
JournalChirality
Volume22
Issue number1
DOIs
Publication statusPublished - Jan 2010

Fingerprint

Lactams
Amylose
Stereoisomerism
Cellulose
Liquids
Carbamates
Enantiomers

Keywords

  • β-lactams
  • AmyCoat™ column
  • CelluCoat™ Column
  • Column liquid chromatography

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

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title = "Comparison of separation performances of amylose- and cellulose-based stationary phases in the high-performance liquid chromatographic enantioseparation of stereoisomers of β-lactams",
abstract = "High-performance liquid chromatographic methods were developed for the separation of the enantiomers of 19 β-lactams. The direct separations were performed on chiral stationary phases containing either amylose-tris-3,5- dimethylphenyl carbamate, (Kromasil{\circledR} AmyCoat™ column) or cellulose-tris-3,5-dimethylphenyl carbamate, (Kromasil{\circledR} CelluCoat™ column) as chiral selector. The different methods were compared in systematic chromatographic examinations. The separations were carried out with good selectivity and resolution. The AmyCoat™ and CelluCoat™ columns appear to be highly complementary. The best separations of bi- and tricyclic b-lactam stereoisomers were obtained with the AmyCoat™ column, whereas the 4-aryl-substituted β-lactams were better separated on the CelluCoat™ column. The elution sequence was determined in all cases; no general rule could be established.",
keywords = "β-lactams, AmyCoat™ column, CelluCoat™ Column, Column liquid chromatography",
author = "Zolt{\'a}n Pataj and I. Ilisz and R. Berkecz and E. Forr{\'o} and F. F{\"u}l{\"o}p and A. P{\'e}ter",
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T1 - Comparison of separation performances of amylose- and cellulose-based stationary phases in the high-performance liquid chromatographic enantioseparation of stereoisomers of β-lactams

AU - Pataj, Zoltán

AU - Ilisz, I.

AU - Berkecz, R.

AU - Forró, E.

AU - Fülöp, F.

AU - Péter, A.

PY - 2010/1

Y1 - 2010/1

N2 - High-performance liquid chromatographic methods were developed for the separation of the enantiomers of 19 β-lactams. The direct separations were performed on chiral stationary phases containing either amylose-tris-3,5- dimethylphenyl carbamate, (Kromasil® AmyCoat™ column) or cellulose-tris-3,5-dimethylphenyl carbamate, (Kromasil® CelluCoat™ column) as chiral selector. The different methods were compared in systematic chromatographic examinations. The separations were carried out with good selectivity and resolution. The AmyCoat™ and CelluCoat™ columns appear to be highly complementary. The best separations of bi- and tricyclic b-lactam stereoisomers were obtained with the AmyCoat™ column, whereas the 4-aryl-substituted β-lactams were better separated on the CelluCoat™ column. The elution sequence was determined in all cases; no general rule could be established.

AB - High-performance liquid chromatographic methods were developed for the separation of the enantiomers of 19 β-lactams. The direct separations were performed on chiral stationary phases containing either amylose-tris-3,5- dimethylphenyl carbamate, (Kromasil® AmyCoat™ column) or cellulose-tris-3,5-dimethylphenyl carbamate, (Kromasil® CelluCoat™ column) as chiral selector. The different methods were compared in systematic chromatographic examinations. The separations were carried out with good selectivity and resolution. The AmyCoat™ and CelluCoat™ columns appear to be highly complementary. The best separations of bi- and tricyclic b-lactam stereoisomers were obtained with the AmyCoat™ column, whereas the 4-aryl-substituted β-lactams were better separated on the CelluCoat™ column. The elution sequence was determined in all cases; no general rule could be established.

KW - β-lactams

KW - AmyCoat™ column

KW - CelluCoat™ Column

KW - Column liquid chromatography

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U2 - 10.1002/chir.20714

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