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Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions

Palma, Aniello, Artelsmair, Markus, Wu, Guanglu, Lu, Xiaoyong, Barrow, Steven J., Uddin, Najib, Rosta, Edina, Masson, Eric, Scherman, Oren A. (2017) Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions. Angewandte Chemie International Edition, 56 (49). pp. 15688-15692. ISSN 1433-7851. (doi:10.1002/anie.201706487) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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Official URL
https://doi.org/10.1002/anie.201706487

Abstract

The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbit[7]uril (CB[7]) 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[7] 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.

Item Type: Article
DOI/Identification number: 10.1002/anie.201706487
Subjects: Q Science > QD Chemistry > QD431 Organic Chemistry- Biochemistry- Proteins, peptides, amino acids
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Aniello Palma
Date Deposited: 22 Nov 2017 10:47 UTC
Last Modified: 13 Jan 2020 09:57 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/64606 (The current URI for this page, for reference purposes)
Palma, Aniello: https://orcid.org/0000-0001-9626-4390
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