PuSH - Publication Server of Helmholtz Zentrum München

Export: TXT Text RIS Endnote (RIS) BIB BibTeX
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)
DOI
Open Access Green as soon as Postprint is submitted to ZB.
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.
Impact Factor
Scopus SNIP
Web of Science
Times Cited
Scopus
Cited By
Altmetric
1.230
0.000
9
13
Tags
Annotations
Special Publikation
Hide on homepage

Edit extra information
Edit own tags
Private
Edit own annotation
Private
Hide on publication lists
on hompage
Mark as special
publikation
Publication type Article: Journal article
Document type Scientific Article
Keywords Column liquid chromatography; Asymmetric induction; ß-Carbolines; Diastereomeric derivatives; Conformational analysis
Language english
Publication Year 2003
HGF-reported in Year 0
ISSN (print) / ISBN 0009-5893
e-ISSN 1612-1112
Journal Chromatographia
Quellenangaben Volume: 57, Issue: 3, Pages: 147-153 Article Number: , Supplement: ,
Publisher Springer
Reviewing status Peer reviewed
Institute(s) Institute of Ecological Chemistry (IOEC)
PSP Element(s) G-505100-004
DOI 10.1007/BF02491708
Erfassungsdatum 2003-03-19
[➜Report correction]