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Fekete, J.* ; Milen, M.* ; Hazai, L.* ; Poppe, L.* ; Szantay, Cs.* ; Kettrup, A. ; Gebefügi, I.

Comparative Study on Separation of Diastereomers by HPLC.

Chromatographia 57, 147-153 (2003)
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Open Access Green möglich sobald Postprint bei der ZB eingereicht worden ist.
Reversed (RP-HPLC) and normal phase chromatographic (NP-HPLC) separations have been developed for diastereomers ofN-acyl-1-methyl-1,2,3,4-tetrahydo-β-carbolines which are acylated derivatives of simple natural β-carboline alkaloids. Separations of derivatives having different acyl moieties in theO,O-diacyl-tartaric acid ester subtituent differed remarkably. Little or no resolution in either NP-HPLC or RP-HPLC could be achieved with the diacetyl-tartrate derivative. Base-line separation by RP-HPLC but no separation by NP-HPLC was possible with the bulkier and more apolar dipivaloyl derivative. Retention order of the bis-benzoylated diastereomers was reversed and separation time increased dramatically by RP-HPLC. Good separation of the medium polarity, but rigid,N-camphanyl derivative by NP-HPLC has been achieved, whereas RP-HPLC could not be used for separation of these diastereomers. Separability of different diastereomers was highly dependent on polarity and rigidity of the derivatizingN-acyl moieties. Conformational analysis by molecular mechanics and comparison of the lowest energy conformational states of the diastereomers was applied to rationalise separation-retention behaviour of stereoisomers by RP-HPLC.
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Publikationstyp Artikel: Journalartikel
Dokumenttyp Wissenschaftlicher Artikel
Schlagwörter Column liquid chromatography; Asymmetric induction; ß-Carbolines; Diastereomeric derivatives; Conformational analysis
Sprache englisch
Veröffentlichungsjahr 2003
HGF-Berichtsjahr 0
ISSN (print) / ISBN 0009-5893
e-ISSN 1612-1112
Zeitschrift Chromatographia
Quellenangaben Band: 57, Heft: 3, Seiten: 147-153 Artikelnummer: , Supplement: ,
Verlag Springer
Begutachtungsstatus Peer reviewed
Institut(e) Institute of Ecological Chemistry (IOEC)
PSP-Element(e) G-505100-004
DOI 10.1007/BF02491708
Erfassungsdatum 2003-03-19
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