High-performance liquid chromatographic methods for separation of the isomers of β-amino acids possessing bicyclo[2.2.1]heptane or heptene skeletons

Gabriella Török, A. Péter, P. Csomós, Liisa T. Kanerva, F. Fülöp

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Reversed-phase high-performance liquid chromatographic methods were developed for separation and identification of the enantiomers of bicyclic β-amino acids: racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo- (1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-bicyclo[2.2.1]heptane-2-carboxylic acids and racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo-(1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-5-bicyclo[2.2.1]heptene-2-carboxylic acids. The enantioselective separations were carried out in two ways: separation of the diastereomers formed by precolumn derivatization with the chiral derivatizing reagents: 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) and 2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl isothiocyanate, and direct separation by the application of a chiral stationary phase, Crownpak CR(+). The results of the methods were compared and optimal conditions were developed in systematic chromatographic examinations.

Original languageEnglish
Pages (from-to)177-186
Number of pages10
JournalJournal of Chromatography A
Volume797
Issue number1-2
DOIs
Publication statusPublished - Feb 27 1998

Fingerprint

Carboxylic Acids
Skeleton
Isomers
Amino Acids
Liquids
Amides
Alanine
Enantiomers
bicyclo(2.2.1)heptene
Marfey's reagent
isothiocyanic acid

Keywords

  • Amino acids
  • Bicycloheptane amino acids
  • Derivatization, LC
  • Enantiomer separation
  • Mobile phase composition

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

@article{f327a1bd7c2b4d36aa70b5ed031e0767,
title = "High-performance liquid chromatographic methods for separation of the isomers of β-amino acids possessing bicyclo[2.2.1]heptane or heptene skeletons",
abstract = "Reversed-phase high-performance liquid chromatographic methods were developed for separation and identification of the enantiomers of bicyclic β-amino acids: racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo- (1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-bicyclo[2.2.1]heptane-2-carboxylic acids and racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo-(1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-5-bicyclo[2.2.1]heptene-2-carboxylic acids. The enantioselective separations were carried out in two ways: separation of the diastereomers formed by precolumn derivatization with the chiral derivatizing reagents: 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) and 2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl isothiocyanate, and direct separation by the application of a chiral stationary phase, Crownpak CR(+). The results of the methods were compared and optimal conditions were developed in systematic chromatographic examinations.",
keywords = "Amino acids, Bicycloheptane amino acids, Derivatization, LC, Enantiomer separation, Mobile phase composition",
author = "Gabriella T{\"o}r{\"o}k and A. P{\'e}ter and P. Csom{\'o}s and Kanerva, {Liisa T.} and F. F{\"u}l{\"o}p",
year = "1998",
month = "2",
day = "27",
doi = "10.1016/S0021-9673(97)00948-5",
language = "English",
volume = "797",
pages = "177--186",
journal = "Journal of Chromatography",
issn = "0021-9673",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - High-performance liquid chromatographic methods for separation of the isomers of β-amino acids possessing bicyclo[2.2.1]heptane or heptene skeletons

AU - Török, Gabriella

AU - Péter, A.

AU - Csomós, P.

AU - Kanerva, Liisa T.

AU - Fülöp, F.

PY - 1998/2/27

Y1 - 1998/2/27

N2 - Reversed-phase high-performance liquid chromatographic methods were developed for separation and identification of the enantiomers of bicyclic β-amino acids: racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo- (1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-bicyclo[2.2.1]heptane-2-carboxylic acids and racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo-(1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-5-bicyclo[2.2.1]heptene-2-carboxylic acids. The enantioselective separations were carried out in two ways: separation of the diastereomers formed by precolumn derivatization with the chiral derivatizing reagents: 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) and 2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl isothiocyanate, and direct separation by the application of a chiral stationary phase, Crownpak CR(+). The results of the methods were compared and optimal conditions were developed in systematic chromatographic examinations.

AB - Reversed-phase high-performance liquid chromatographic methods were developed for separation and identification of the enantiomers of bicyclic β-amino acids: racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo- (1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-bicyclo[2.2.1]heptane-2-carboxylic acids and racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo-(1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-5-bicyclo[2.2.1]heptene-2-carboxylic acids. The enantioselective separations were carried out in two ways: separation of the diastereomers formed by precolumn derivatization with the chiral derivatizing reagents: 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) and 2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl isothiocyanate, and direct separation by the application of a chiral stationary phase, Crownpak CR(+). The results of the methods were compared and optimal conditions were developed in systematic chromatographic examinations.

KW - Amino acids

KW - Bicycloheptane amino acids

KW - Derivatization, LC

KW - Enantiomer separation

KW - Mobile phase composition

UR - http://www.scopus.com/inward/record.url?scp=0032570958&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032570958&partnerID=8YFLogxK

U2 - 10.1016/S0021-9673(97)00948-5

DO - 10.1016/S0021-9673(97)00948-5

M3 - Article

AN - SCOPUS:0032570958

VL - 797

SP - 177

EP - 186

JO - Journal of Chromatography

JF - Journal of Chromatography

SN - 0021-9673

IS - 1-2

ER -