Search: id:"swepub:oai:DiVA.org:su-149845" >
Regioselective para...
Regioselective para-Carboxylation of Catechols with a Prenylated Flavin Dependent Decarboxylase
-
Payer, Stefan E. (author)
-
Marshall, Stephen A. (author)
-
Bärland, Natalie (author)
-
show more...
-
- Sheng, Xiang (author)
- Stockholms universitet,Institutionen för organisk kemi
-
Reiter, Tamara (author)
-
Dordic, Andela (author)
-
Steinkellner, Georg (author)
-
Wuensch, Christiane (author)
-
Kaltwasser, Susann (author)
-
Fisher, Karl (author)
-
Rigby, Stephen E. J. (author)
-
Macheroux, Peter (author)
-
Vonck, Janet (author)
-
Gruber, Karl (author)
-
Faber, Kurt (author)
-
- Himo, Fahmi (author)
- Stockholms universitet,Institutionen för organisk kemi
-
Leys, David (author)
-
Pavkov-Keller, Tea (author)
-
Glueck, Silvia M. (author)
-
show less...
-
(creator_code:org_t)
- 2017-10-02
- 2017
- English.
-
In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 56:44, s. 13893-13897
- Related links:
-
https://doi.org/10.1...
-
show more...
-
https://onlinelibrar...
-
https://urn.kb.se/re...
-
https://doi.org/10.1...
-
show less...
Abstract
Subject headings
Close
- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- biocatalysis
- carboxylation
- catechols
- prenylated FMN
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
To the university's database
- By the author/editor
-
Payer, Stefan E.
-
Marshall, Stephe ...
-
Bärland, Natalie
-
Sheng, Xiang
-
Reiter, Tamara
-
Dordic, Andela
-
show more...
-
Steinkellner, Ge ...
-
Wuensch, Christi ...
-
Kaltwasser, Susa ...
-
Fisher, Karl
-
Rigby, Stephen E ...
-
Macheroux, Peter
-
Vonck, Janet
-
Gruber, Karl
-
Faber, Kurt
-
Himo, Fahmi
-
Leys, David
-
Pavkov-Keller, T ...
-
Glueck, Silvia M ...
-
show less...
- About the subject
-
- NATURAL SCIENCES
-
NATURAL SCIENCES
-
and Chemical Science ...
- Articles in the publication
-
Angewandte Chemi ...
- By the university
-
Stockholm University