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Chirality. 2017 Jun;29(6):247-256. doi: 10.1002/chir.22703. Epub 2017 Apr 25.

Resolution, determination of enantiomeric purity and chiral recognition mechanism of new xanthone derivatives on (S,S)-whelk-O1 stationary phase.

Author information

1
Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Porto, Portugal.
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Edifício do Terminal de Cruzeiros do Porto de Leixões, Matosinhos, Portugal.
3
CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde (IINFACTS), Gandra, Portugal.

Abstract

The enantioresolution and determination of the enantiomeric purity of 32 new xanthone derivatives, synthesized in enantiomerically pure form, were investigated on (S,S)-Whelk-O1 chiral stationary phase (CSP). Enantioselectivity and resolution (α and RS ) with values ranging from 1.41-6.25 and from 1.29-17.20, respectively, were achieved. The elution was in polar organic mode with acetonitrile/methanol (50:50 v/v) as mobile phase and, generally, the (R)-enantiomer was the first to elute. The enantiomeric excess (ee) for all synthesized xanthone derivatives was higher than 99%. All the enantiomeric pairs were enantioseparated, even those without an aromatic moiety linked to the stereogenic center. Computational studies for molecular docking were carried out to perform a qualitative analysis of the enantioresolution and to explore the chiral recognition mechanisms. The in silico results were consistent with the chromatographic parameters and elution orders. The interactions between the CSP and the xanthone derivatives involved in the chromatographic enantioseparation were elucidated.

KEYWORDS:

chiral derivatives of xanthones; chiral recognition; docking; enantiomeric purity; enantioselectivity; whelk-O1 column

PMID:
28439971
DOI:
10.1002/chir.22703
[Indexed for MEDLINE]

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