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

Aniello Palma; Markus Artelsmair; Guanglu Wu; Xiaoyong Lu; Steven J. Barrow; Najib Uddin; Edina Rosta; Eric Masson; Oren A. Scherman

doi:10.1002/anie.201706487

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

Aniello Palma, Markus Artelsmair, Guanglu Wu, Xiaoyong Lu, Steven J. Barrow, Najib Uddin, Edina Rosta, Eric Masson^*, Oren A. Scherman

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

75 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6
Number of pages	1
Journal	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume	56
DOIs	https://doi.org/10.1002/anie.201706487
Publication status	Published - 3 Nov 2017

Keywords

Biomimetic catalysts
Cucurbit[7]uril
Diels-Alder reactions
Enzyme mimics

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10.1002/anie.201706487

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title = "Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions",

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.",

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AU - Palma, Aniello

AU - Artelsmair, Markus

AU - Wu, Guanglu

AU - Lu, Xiaoyong

AU - Barrow, Steven J.

AU - Uddin, Najib

AU - Rosta, Edina

AU - Masson, Eric

AU - Scherman, Oren A.

PY - 2017/11/3

Y1 - 2017/11/3

N2 - 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.

AB - 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.

KW - Biomimetic catalysts

KW - Cucurbit[7]uril

KW - Diels-Alder reactions

KW - Enzyme mimics

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ER -

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

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