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Phytosterol Recognition via Rationally Designed Molecularly Imprinted Polymers

Centre for Green Chemistry and Australian Centre for Research on Separation Science, School of Chemistry, Monash University, Melbourne, VIC 3800, Australia
Current Address: School of Agricultural and Wine Sciences, Faculty of Science, Charles Sturt University, Wagga Wagga, NSW 2678, Australia.
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Received: 29 December 2017 / Revised: 4 February 2018 / Accepted: 4 February 2018 / Published: 12 February 2018
(This article belongs to the Special Issue Molecularly Imprinted Polymers—Molecular Recognition)
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Abstract

Molecularly imprinted polymers (MIPs) prepared via a semi-covalent imprinting strategy using stigmasteryl methacrylate as a polymerisable template have been evaluated by static binding methods for their ability to selectively capture other valuable phytosterol targets, including campesterol and brassicasterol. Design criteria based on molecular modelling procedures and interaction energy calculations were employed to aid the selection of the co-monomer type, as well as the choice of co-monomer:template ratios for the formation of the pre-polymerisation complex. These novel hybrid semi-covalently imprinted polymers employed N,N′-dimethylacryl-amide (N,N′-DMAAM) as the functional co-monomer and displayed specific binding capacities in the range 5.2–5.9 mg sterol/g MIP resin. Their binding attributes and selectivities towards phytosterol compounds were significantly different to the corresponding MIPs prepared via non-covalent procedures or when compared to non-imprinted polymers. Cross-reactivity studies using stigmasterol, ergosterol, cholesterol, campesterol, and brassicasterol as single analytes revealed the importance of the A-ring C-3-β-hydroxyl group and the orientational preferences of the D-ring alkyl chain structures in their interaction in the templated cavity with the N,N′-dimethylamide functional groups of the MIP. Finally, to obtain useful quantities of both campersterol and brassicasterol for these investigations, improved synthetic routes have been developed to permit the conversion of the more abundant, lower cost stigmasterol via a reactive aldehyde intermediate to these other sterols. View Full-Text
Keywords: phytosterols; molecular modelling; interaction energies; molecularly imprinted polymers; selectivity phytosterols; molecular modelling; interaction energies; molecularly imprinted polymers; selectivity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Schwarz, L.J.; Leung, B.K.Y.; Danylec, B.; Harris, S.J.; Boysen, R.I.; Hearn, M.T.W. Phytosterol Recognition via Rationally Designed Molecularly Imprinted Polymers. C 2018, 4, 13.

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