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Regioselective para-Carboxylation of Catechols with a Prenylated Flavin Dependent Decarboxylase
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-6542-6649
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Number of Authors: 192017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 44, p. 13893-13897Article in journal (Refereed) Published
Abstract [en]

The utilization of CO2 as a carbon source for organic synthesis meets the urgent demand for more sustainability in the production of chemicals. Herein, we report on the enzyme-catalyzed para-carboxylation of catechols, employing 3,4-dihydroxybenzoic acid decarboxylases (AroY) that belong to the UbiD enzyme family. Crystal structures and accompanying solution data confirmed that AroY utilizes the recently discovered prenylated FMN (prFMN) cofactor, and requires oxidative maturation to form the catalytically competent prFMN(iminium) species. This study reports on the in vitro reconstitution and activation of a prFMN-dependent enzyme that is capable of directly carboxylating aromatic catechol substrates under ambient conditions. A reaction mechanism for the reversible decarboxylation involving an intermediate with a single covalent bond between a quinoid adduct and cofactor is proposed, which is distinct from the mechanism of prFMN-associated 1,3-dipolar cycloadditions in related enzymes.

Place, publisher, year, edition, pages
2017. Vol. 56, no 44, p. 13893-13897
Keywords [en]
biocatalysis, carboxylation, catechols, prenylated FMN
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-149845DOI: 10.1002/anie.201708091ISI: 000413314800066PubMedID: 28857436OAI: oai:DiVA.org:su-149845DiVA, id: diva2:1164822
Available from: 2017-12-12 Created: 2017-12-12 Last updated: 2017-12-12Bibliographically approved

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Payer, Stefan E.Marshall, Stephen A.Sheng, XiangFisher, KarlRigby, Stephen E. J.Gruber, KarlHimo, FahmiPavkov-Keller, Tea
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