High-performance liquid chromatographic separation of enantiomers of cyclic 1,3-amino alcohol derivatives

Mária Péter, A. Péter, Johan Van Der Eycken, P. Csomós, G. Bernáth, F. Fülöp

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol derivatives. Direct separation was carried out on a cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD) stationary phase, which allowed the simultaneous separation of enantiomers of alcohol and ester analogues of the amino alcohols. Derivatization of amino alcohols with 1-fluoro-2,4-dinitrophenyl-5-l-alaninamide produced diastereomers which were separable with high resolution (R(s)>5), whereas derivatives with 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate coeluted. The absolute configurations and elution sequences of the enantiomers were determined by both methods. Copyright (C) 1998 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)123-129
Number of pages7
JournalJournal of Chromatography A
Volume816
Issue number2
DOIs
Publication statusPublished - Aug 14 1998

Fingerprint

Amino Alcohols
Enantiomers
Methanol
Derivatives
Liquids
Esters
Alcohols
cellulose tris-3,5-dimethylphenyl-carbamate
cyclohexene
Marfey's reagent
isothiocyanic acid

Keywords

  • 2-Amino-4-cyclohexene-1-methanol
  • 2-Aminocyclohexane-1-methanol
  • Cyclic amino alcohols
  • Enantiomer separation

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

High-performance liquid chromatographic separation of enantiomers of cyclic 1,3-amino alcohol derivatives. / Péter, Mária; Péter, A.; Van Der Eycken, Johan; Csomós, P.; Bernáth, G.; Fülöp, F.

In: Journal of Chromatography A, Vol. 816, No. 2, 14.08.1998, p. 123-129.

Research output: Contribution to journalArticle

@article{8271342dbc6c4cd4a6c875aaa2736aa6,
title = "High-performance liquid chromatographic separation of enantiomers of cyclic 1,3-amino alcohol derivatives",
abstract = "Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol derivatives. Direct separation was carried out on a cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD) stationary phase, which allowed the simultaneous separation of enantiomers of alcohol and ester analogues of the amino alcohols. Derivatization of amino alcohols with 1-fluoro-2,4-dinitrophenyl-5-l-alaninamide produced diastereomers which were separable with high resolution (R(s)>5), whereas derivatives with 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate coeluted. The absolute configurations and elution sequences of the enantiomers were determined by both methods. Copyright (C) 1998 Elsevier Science B.V.",
keywords = "2-Amino-4-cyclohexene-1-methanol, 2-Aminocyclohexane-1-methanol, Cyclic amino alcohols, Enantiomer separation",
author = "M{\'a}ria P{\'e}ter and A. P{\'e}ter and {Van Der Eycken}, Johan and P. Csom{\'o}s and G. Bern{\'a}th and F. F{\"u}l{\"o}p",
year = "1998",
month = "8",
day = "14",
doi = "10.1016/S0021-9673(98)00471-3",
language = "English",
volume = "816",
pages = "123--129",
journal = "Journal of Chromatography",
issn = "0021-9673",
publisher = "Elsevier",
number = "2",

}

TY - JOUR

T1 - High-performance liquid chromatographic separation of enantiomers of cyclic 1,3-amino alcohol derivatives

AU - Péter, Mária

AU - Péter, A.

AU - Van Der Eycken, Johan

AU - Csomós, P.

AU - Bernáth, G.

AU - Fülöp, F.

PY - 1998/8/14

Y1 - 1998/8/14

N2 - Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol derivatives. Direct separation was carried out on a cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD) stationary phase, which allowed the simultaneous separation of enantiomers of alcohol and ester analogues of the amino alcohols. Derivatization of amino alcohols with 1-fluoro-2,4-dinitrophenyl-5-l-alaninamide produced diastereomers which were separable with high resolution (R(s)>5), whereas derivatives with 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate coeluted. The absolute configurations and elution sequences of the enantiomers were determined by both methods. Copyright (C) 1998 Elsevier Science B.V.

AB - Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol derivatives. Direct separation was carried out on a cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD) stationary phase, which allowed the simultaneous separation of enantiomers of alcohol and ester analogues of the amino alcohols. Derivatization of amino alcohols with 1-fluoro-2,4-dinitrophenyl-5-l-alaninamide produced diastereomers which were separable with high resolution (R(s)>5), whereas derivatives with 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate coeluted. The absolute configurations and elution sequences of the enantiomers were determined by both methods. Copyright (C) 1998 Elsevier Science B.V.

KW - 2-Amino-4-cyclohexene-1-methanol

KW - 2-Aminocyclohexane-1-methanol

KW - Cyclic amino alcohols

KW - Enantiomer separation

UR - http://www.scopus.com/inward/record.url?scp=0038915272&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0038915272&partnerID=8YFLogxK

U2 - 10.1016/S0021-9673(98)00471-3

DO - 10.1016/S0021-9673(98)00471-3

M3 - Article

AN - SCOPUS:0038915272

VL - 816

SP - 123

EP - 129

JO - Journal of Chromatography

JF - Journal of Chromatography

SN - 0021-9673

IS - 2

ER -