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pre-FAB SIGNED

Prenylated-flavins: Application and Biochemistry

Total Cost €

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EC-Contrib. €

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Partnership

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 pre-FAB project word cloud

Explore the words cloud of the pre-FAB project. It provides you a very rough idea of what is the project "pre-FAB" about.

hints    aryl    benzene    organic    bacterial    ubiquinone    dipolarophile    suggests    decarboxylation    de    relationships    commodity    supports    sufficient    explore    flavoenzymes    oxidative    artificial    maturation    ylide    binds    our    latter    biodegradation    subunit    dipolar    takes    cycloaddition    cofactor    azomethine    enzymes    monoxygenases    create    alkene    integral    ambitiously    builds    ultimately    altogether    couple    aromatic    monoxygenase    microbial    prenyltransferase    plays    reversible    seek    ubix    biosynthesis    data    acts    enzyme    family    discovered    group    linking    moiety    compounds    unusual    substrates    model    hydrolysis    dependent    c6    enzymatic    function    atp    routes    first    naphthalene    self    evolution    structure    pivotal    carboxylation    harness    catalysis    implicated    dimethylallyl    reaction    ubid    atoms    chemicals    chemistry    hydrocarbon    green    substrate    holo    n5    prfmn    prenylated    flavin   

Project "pre-FAB" data sheet

The following table provides information about the project.

Coordinator
THE UNIVERSITY OF MANCHESTER 

Organization address
address: OXFORD ROAD
city: MANCHESTER
postcode: M13 9PL
website: www.manchester.ac.uk

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
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 Coordinator Country United Kingdom [UK]
 Total cost 2˙494˙328 €
 EC max contribution 2˙494˙328 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2015-AdG
 Funding Scheme ERC-ADG
 Starting year 2016
 Duration (year-month-day) from 2016-09-01   to  2021-08-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    THE UNIVERSITY OF MANCHESTER UK (MANCHESTER) coordinator 2˙494˙328.00

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 Project objective

Our group has recently discovered a new type of cofactor: a prenylated-flavin that has azomethine ylide properties. This cofactor is an integral part of the widespread ubiD/ubiX system. The latter is implicated in the non-oxidative reversible decarboxylation of aromatic substrates, and plays a pivotal role in bacterial ubiquinone biosynthesis or microbial biodegradation of aromatic compounds. We established UbiX acts as a novel flavin prenyltransferase, linking a dimethylallyl moiety to the flavin N5 and C6 atoms. Formation of the holo-UbiD enzyme involves oxidative maturation of the new cofactor, creating the novel azomethine ylide moiety. The dipolarophile substrate binds directly above the azomethine ylide group, and our data strongly suggests 1,3-dipolar cycloaddition chemistry supports reversible decarboxylation in these enzymes. While 1,3-dipolar cycloaddition is commonly used in organic chemistry, this presents the first example of an enzymatic 1,3-dipolar cycloaddition reaction. Our model for UbiD catalysis hints at new routes in alkene hydrocarbon production or aryl (de)carboxylation.

The current application builds ambitiously on these results and takes the project altogether to another level: we seek to investigate structure/function of relationships of the wider UbiD family, ultimately including the multi-subunit enzymes that couple ATP-hydrolysis to benzene or naphthalene carboxylation. Furthermore, we will explore and harness the unusual properties of the prenylated flavin, through targeted evolution of (monoxygenase) flavoenzymes to create artificial prFMN-dependent self-sufficient monoxygenases. Our approach seeks to harness both the UbiD and the artificial prFMN-dependent enzymes in novel green routes to commodity chemicals.

 Publications

year authors and title journal last update
List of publications.
2018 Samuel S. Bailey, Karl A. P. Payne, Karl Fisher, Stephen A. Marshall, Matthew J. Cliff, Reynard Spiess, David A. Parker, Stephen E. J. Rigby, David Leys
The role of conserved residues in Fdc decarboxylase in prenylated flavin mononucleotide oxidative maturation, cofactor isomerization, and catalysis
published pages: 2272-2287, ISSN: 0021-9258, DOI: 10.1074/jbc.RA117.000881
Journal of Biological Chemistry 293/7 2019-09-06
2017 Stefan E. Payer, Stephen A. Marshall, Natalie Bärland, Xiang Sheng, Tamara Reiter, Andela Dordic, Georg Steinkellner, Christiane Wuensch, Susann Kaltwasser, Karl Fisher, Stephen E. J. Rigby, Peter Macheroux, Janet Vonck, Karl Gruber, Kurt Faber, Fahmi Himo, David Leys, Tea Pavkov-Keller, Silvia M. Glueck
Regioselective para -Carboxylation of Catechols with a Prenylated Flavin Dependent Decarboxylase
published pages: 13893-13897, ISSN: 1433-7851, DOI: 10.1002/anie.201708091
Angewandte Chemie International Edition 56/44 2019-09-06
2018 Godwin A. Aleku, Christoph Prause, Ruth T. Bradshaw-Allen, Katharina Plasch, Silvia M. Glueck, Samuel S. Bailey, Karl A. P. Payne, David A. Parker, Kurt Faber, David Leys
Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases
published pages: 3736-3745, ISSN: 1867-3880, DOI: 10.1002/cctc.201800643
ChemCatChem 10/17 2019-09-06
2018 David Leys
Flavin metamorphosis: cofactor transformation through prenylation
published pages: 117-125, ISSN: 1367-5931, DOI: 10.1016/j.cbpa.2018.09.024
Current Opinion in Chemical Biology 47 2019-09-06
2019 Karl A.P. Payne, Stephen A. Marshall, Karl Fisher, Matthew J. Cliff, Diego M. Cannas, Cunyu Yan, Derren J. Heyes, David A. Parker, Igor Larrosa, David Leys
Enzymatic Carboxylation of 2-Furoic Acid Yields 2,5-Furandicarboxylic Acid (FDCA)
published pages: 2854-2865, ISSN: 2155-5435, DOI: 10.1021/acscatal.8b04862
ACS Catalysis 9/4 2019-09-06

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