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

• Type: Article in International Scientific Journal
• Date: 2013

Authors

Carla Fernandes (Author) FFUP; Andreia Palmeira (Author) Other; Alexandre Santos (Author) Other; Maria Elizabeth Tiritan (Author) Other; Carlos Afonso (Author) FFUP; Madalena M Pinto (Author) FFUP

Journal

Title: Chirality

Vol. 25

Pages: 89-100

ISSN: 0899-0042

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 29 Citations

Scopus - 30 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-002-0YP

DOI: 10.1002/chir.22112

Abstract (EN): 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 CSPCDX 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 CSPCDX interactions. Chirality 25:89100, 2013.(c) 2012 Wiley Periodicals, Inc.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 12