Clean synthesis of molecular recognition polymeric materials with chiral sensing capability using supercritical fluid technology. Application as HPLC stationary phases

abstract

Molecularly imprinted polymers (MIPs) of poly(ethylene glycol dimethacrylate) and poly(N-isopropylacrylamide-co-ethylene glycol dimethacrylate) were synthesized for the first time in supercritical carbon dioxide (scCO(2)), using Boc-L-tryptophan as template. Supercritical fluid technology provides a clean and one-step synthetic route for the preparation of affinity polymeric materials with sensing capability for specific molecules. The polymeric materials were tested as stationary HPLC phases for the enantiomeric separation of L- and D-tryptophan. HPLC results prove that the synthesized MIPs are able to recognize the template molecule towards its enantiomer which opens up potential applications in chromatographic chiral separation. (C) 2009 Elsevier B.V. All rights reserved.

keywords

IMPRINTED POLYMERS; CARBON-DIOXIDE; SEPARATION; CHROMATOGRAPHY; TEMPERATURE; PERFORMANCE; EXTRACTION; ENANTIOMER

subject category

Biophysics; Biotechnology & Applied Microbiology; Chemistry; Electrochemistry; Science & Technology - Other Topics

authors

da Silva, MS; Vao, ER; Temtem, M; Mafra, L; Caldeira, J; Aguiar-Ricardo, A; Casimiro, T

our authors

acknowledgements

The authors would like to thank Fundacao para a Ciencia e Tecnologia (FCT-Lisbon) for financial support through projects PTDC/QUI/66086/2006 and PTDC/CrM/70513/2006, and doctoral grant SFRH/BD/31085/2006 (M.S.S.), FEDER, FSE and POCTI. The Portuguese NMR Network is acknowledged for granting access to the NMR equipment.

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