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Enantioresolution of Chiral Derivatives of Xanthones on ( S , S )‐Whelk‐O1 and l ‐Phenylglycine Stationary Phases and Chiral Recognition Mechanism by Docking Approach for ( S , S )‐Whelk‐O1
Author(s) -
Fernandes Carla,
Palmeira Andreia,
Santos Alexandre,
Tiritan Maria Elizabeth,
Afonso Carlos,
Pinto Madalena M.
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22112
Subject(s) - chemistry , stereocenter , enantiomer , moiety , docking (animal) , elution , stereochemistry , enantioselective synthesis , chiral column chromatography , combinatorial chemistry , computational chemistry , chromatography , organic chemistry , medicine , nursing , catalysis
The resolution of seven enantiomeric pairs of chiral derivatives of xanthones (CDXs) on ( S , S )‐Whelk‐O1 and l ‐phenylglycine chiral stationary phases (CSPs) was systematically investigated using multimodal elution conditions (normal‐phase, polar‐organic, and reversed‐phase). The ( S,S )‐Whelk‐O1 CSP, under polar‐organic conditions, demonstrated a very good power of resolution for the CDXs possessing an aromatic moiety linked to the stereogenic center with separation factor and resolution factor ranging from 1.91 to 7.55 and from 6.71 to 24.16, respectively. The chiral recognition mechanisms were also investigated for ( S , S )‐Whelk‐O1 CSP by molecular docking technique. Data regarding the CSP–CDX molecular conformations and interactions were retrieved. These results were in accordance with the experimental chromatographic parameters regarding enantioselectivity and enantiomer elution order. The results of the present study fulfilled the initial objectives of enantioselective studies of CDXs and elucidation of intermolecular CSP–CDX interactions. Chirality 25:89–100, 2013 . © 2012 Wiley Periodicals, Inc.