Journal
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
Volume 58, Issue 1-4, Pages 110-117Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.molcatb.2008.12.002
Keywords
Diels-Alder; Enzyme mimic; Molecularly imprinted polymer; Transition state analogue
Funding
- Swedish Research Council (VR)
- Swedish Knowledge Foundation (KKS)
- Graninge Foundation
- Sparbank Kronan Foundation
- University of Kalmar
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A series of synthetic polymers were designed and synthesized for enhancing the rate of the Diels-Alder cycloaddition reaction of 1,3-butadiene carbamic acid benzyl ester (11) and N,N-dimethyl acrylamide (2), to yield the corresponding endo- (3) and exo- (4) reaction products. Putative transition state analogues (TSAs) for the endo- (5) and exo- (6) reaction pathways were used as templates for the synthesis of molecularly imprinted methacrylic acid (MAA)-divinylbenzene (DVB) copolymers. The polymer system utilized was selected based upon a series of H-1 NMR studies of complex formation between template and a functional monomer analogue (K-d (app) approximate to 70 mM, d(8)-toluene, 293 K). Batch binding studies revealed that the imprinted polymers were selective for the TSA corresponding to the template used in the polymer synthesis. Studies on the influence of the polymers on the catalysis of the reaction of 1 and 2 demonstrated a 20-fold enhancement of the rate of the reaction relative to the solution reaction. A surprising temperature dependence of the reaction of 1 and 2 in the presence of the polymers was observed, which provides support for the role of template-functional monomer complexes in the catalysis of the Diels-Alder reaction. (C) 2009 Elsevier B.V. All rights reserved.
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