Cucurbituril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions
Angewandte Chemie - International Edition
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Palma, A., Artelsmair, M., Guanglu, W., Barrow, S., Lu, X., Uddin, N., Rosta, E., et al. (2017). Cucurbituril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions. Angewandte Chemie - International Edition, 56 (49), 15688-15692. https://doi.org/10.1002/anie.201706487
The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbituril (CB) can catalyse Diels–Alder reactions for a number of substituted and unreactive N-allyl-2-furfurylamines under biomimetic conditions, without the need for protecting groups, yielding powerful synthons in previously unreported mild conditions. CB rearranges the substrate in a highly reactive conformation and shields it from the aqueous environment, thereby mimicking the mode of action of a natural Diels–Alderase. These findings can be directly applied to the phenomenon of product inhibition observed in natural Diels–Alderase enzymes, and pave the way toward the development of novel, supramolecular-based green catalysts.
biomimetic catalysts, cucurbituril, Diels–Alder reactions, enzyme mimics
Is supplemented by: https://doi.org/10.17863/CAM.12345
O.A.S. and A.P. acknowledge an ERC starting investigator grant (ASPiRe 240629) and EPSRC Programme Grant (NOtCH, EP/L027151/1) for the support, G.W. thanks the Leverhulme Trust (Natural material innovation for sustainable living) for the support, S.J.B. thanks the European Commission for a Marie Curie Fellowship (NANOSPHERE, 658360), E.R. gratefully acknowledges financial support from EPSRC (EP/N020669/1), E.M. and X.L. acknowledge the American Chemical Society Petroleum Research Fund (PRF No. 51053-ND4), the Department of Chemistry and Biochemistry, the College of Arts and Sciences and the Vice President for Research at Ohio University.
European Research Council (240629)
European Commission (658360)
External DOI: https://doi.org/10.1002/anie.201706487
This record's URL: https://www.repository.cam.ac.uk/handle/1810/270356