Enantiomeric separation of racemic neolignans on chiralcel OD and determination of their absolute configuration with online circular dichroism

Krisztina Kónya, Attila Kiss-Szikszai, Tibor Kurtán, Sándor Antus

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Effective enantiomeric separations of erythro- and threo-8.O.4′- neolignans with different aromatic substitution pattern (1a-i, 2a-i) are achieved on the commercially available chiral stationary phase cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD). It is shown that the chiral recognition of the stationary phase is significantly dependent on the substitution pattern of the racemic compounds. Online liquid chromatography (LC)-circular dichroism (CD) analysis allows for the establishment of a correlation between the absolute configuration of the separated erythro-8.O.4′-neolignans and their characteristic CD transitions, which could be used to determine or revise the configuration of previously isolated erythro-8.O.4′-neolignans. Although the absolute configurations of threo-isomers is not determined unambiguously from the LC-CD analysis, it is proven that both their elution order and chiroptical properties are significantly influenced by the substitution pattern of the aromatic rings.

Original languageEnglish
Pages (from-to)478-483
Number of pages6
JournalJournal of chromatographic science
Volume42
Issue number9
DOIs
Publication statusPublished - Oct 2004

ASJC Scopus subject areas

  • Analytical Chemistry

Fingerprint Dive into the research topics of 'Enantiomeric separation of racemic neolignans on chiralcel OD and determination of their absolute configuration with online circular dichroism'. Together they form a unique fingerprint.

  • Cite this