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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2013

Autores

Carla Fernandes (Autor) FFUP; Andreia Palmeira (Autor) Outra; Alexandre Santos (Autor) Outra; M E Tiritan (Autor) FFUP; Carlos Afonso (Autor) FFUP; Madalena M Pinto (Autor) FFUP

Revista

Título: Chirality

Vol. 25

Páginas: 89-100

ISSN: 0899-0042

Editora: Wiley-Blackwell

Indexação

ISI Web of Knowledge - 31 Citações

Scopus - 33 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 12