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Molecules 2018, 23(1), 142; https://doi.org/10.3390/molecules23010142

Enantiomeric Resolution and Docking Studies of Chiral Xanthonic Derivatives on Chirobiotic Columns

1
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4050-208 Matosinhos, Portugal
3
Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
4
CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde (IINFACTS), Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal
*
Authors to whom correspondence should be addressed.
Received: 29 November 2017 / Revised: 6 January 2018 / Accepted: 8 January 2018 / Published: 11 January 2018
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
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Abstract

A systematic study of enantioresolution of a library of xanthonic derivatives, prepared “in-house”, was successfully carried out with four commercially available macrocyclic glycopeptide-based columns, namely ChirobioticTM T, ChirobioticTM R, ChirobioticTM V and ChirobioticTM TAG. Evaluation was conducted in multimodal elution conditions: normal-phase, polar organic, polar ionic and reversed-phase. The effects of the mobile phase composition, the percentage of organic modifier, the pH of the mobile phase, the nature and concentration of different mobile phase additives on the chromatographic parameters are discussed. ChirobioticTM T and ChirobioticTM V, under normal-phase and reversed-phase modes, respectively, presented the best chromatographic parameters. Considering the importance of understanding the chiral recognition mechanisms associated with the chromatographic enantioresolution, and the scarce data available for macrocyclic glycopeptide-based columns, computational studies by molecular docking were also carried out. View Full-Text
Keywords: ChirobioticTM; docking; enantioresolution; enantioselectivity; molecular recognition; xanthonic derivatives ChirobioticTM; docking; enantioresolution; enantioselectivity; molecular recognition; xanthonic derivatives
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Phyo, Y.Z.; Cravo, S.; Palmeira, A.; Tiritan, M.E.; Kijjoa, A.; Pinto, M.M.M.; Fernandes, C. Enantiomeric Resolution and Docking Studies of Chiral Xanthonic Derivatives on Chirobiotic Columns. Molecules 2018, 23, 142.

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