Chiral effects of alkyl-substituted derivatives of N,O-bismethacryloyl ethanolamine on the performance of one monomer molecularly imprinted polymers (OMNiMIPs) |
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Authors: | LeJeune Jason Spivak David A |
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Institution: | (1) Chemistry Department, Louisiana State University, Baton Rouge, LA 70803, USA |
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Abstract: | New monomers were synthesized and evaluated for their molecular imprinting performance by a recently discovered methodology
referred to as one monomer molecularly imprinted polymers (OMNiMIPs). The structural design of the new monomers was based
on a lead compound methacrylamidoethyl methacrylate (1) used for the synthesis of OMNiMIP1, and introduced alkyl groups of various sizes at the α-amino position of the lead compound.
Enantioselectivity, determined by liquid chromatography, was used to compare the performance of the imprinted polymers. Methyl
substitution provided crosslinker 5 (2-methacrylamidopropyl methacrylate), which upon imprint polymerization afforded OMNiMIP5 with approximately the same enantioselectivity
(α = 3.8) as OMNiMP1 (α = 3.7) made with the lead compound (1). The other two monomers (6 and 7) with larger alkyl substitutions (isopropyl and sec-butyl respectively) resulted in OMNiMIPs with low selectivity values (α = 1.0 and 1.2 respectively). Last, a strong influence
of diastereomeric complexes on OMNiMIP5 selectivity was determined, with L/L and D/D monomer/template pairs giving α values of 3.6–3.8, while L/D and D/L monomer/template pairs had α values of 2.3–2.4. There is no intrinsic enantioselectivity seen for the OMNiMIP5 control polymer
made without template at all, giving an α value of 1.03.
Electronic Supplementary Material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
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Keywords: | Molecular imprinting Resolution OMNiMIPs Crosslinkers Enantioselectivity Chromatography |
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