Literature DB >> 33542397

Crystal structures of non-oxidative decarboxylases reveal a new mechanism of action with a catalytic dyad and structural twists.

Matthias Zeug1,2,3, Nebojsa Markovic4, Cristina V Iancu2, Joanna Tripp3, Mislav Oreb5, Jun-Yong Choe6,7.   

Abstract

Hydroxybenzoic acids, like gallic acid and protocatechuic acid, are highly abundant natural compounds. In biotechnology, they serve as critical precursors for various molecules in heterologous production pathways, but a major bottleneck is these acids' non-oxidative decarboxylation to hydroxybenzenes. Optimizing this step by pathway and enzyme engineering is tedious, partly because of the complicating cofactor dependencies of the commonly used prFMN-dependent decarboxylases. Here, we report the crystal structures (1.5-1.9 Å) of two homologous fungal decarboxylases, AGDC1 from Arxula adenivorans, and PPP2 from Madurella mycetomatis. Remarkably, both decarboxylases are cofactor independent and are superior to prFMN-dependent decarboxylases when heterologously expressed in Saccharomyces cerevisiae. The organization of their active site, together with mutational studies, suggests a novel decarboxylation mechanism that combines acid-base catalysis and transition state stabilization. Both enzymes are trimers, with a central potassium binding site. In each monomer, potassium introduces a local twist in a β-sheet close to the active site, which primes the critical H86-D40 dyad for catalysis. A conserved pair of tryptophans, W35 and W61, acts like a clamp that destabilizes the substrate by twisting its carboxyl group relative to the phenol moiety. These findings reveal AGDC1 and PPP2 as founding members of a so far overlooked group of cofactor independent decarboxylases and suggest strategies to engineer their unique chemistry for a wide variety of biotechnological applications.

Entities:  

Year:  2021        PMID: 33542397     DOI: 10.1038/s41598-021-82660-z

Source DB:  PubMed          Journal:  Sci Rep        ISSN: 2045-2322            Impact factor:   4.379


  30 in total

Review 1.  Yeast factories for the production of aromatic compounds: from building blocks to plant secondary metabolites.

Authors:  Miguel Suástegui; Zengyi Shao
Journal:  J Ind Microbiol Biotechnol       Date:  2016-08-31       Impact factor: 3.346

2.  Pyrogallol, an active compound from the medicinal plant Emblica officinalis, regulates expression of pro-inflammatory genes in bronchial epithelial cells.

Authors:  Elena Nicolis; Ilaria Lampronti; Maria Cristina Dechecchi; Monica Borgatti; Anna Tamanini; Nicoletta Bianchi; Valentino Bezzerri; Irene Mancini; Maria Grazia Giri; Paolo Rizzotti; Roberto Gambari; Giulio Cabrini
Journal:  Int Immunopharmacol       Date:  2008-08-27       Impact factor: 4.932

3.  Purification and characterization of gallic acid decarboxylase from pantoea agglomerans T71

Authors: 
Journal:  Appl Environ Microbiol       Date:  1998-12       Impact factor: 4.792

4.  Biosynthesis of cis,cis-muconic acid and its aromatic precursors, catechol and protocatechuic acid, from renewable feedstocks by Saccharomyces cerevisiae.

Authors:  Christian Weber; Christine Brückner; Sheila Weinreb; Claudia Lehr; Christine Essl; Eckhard Boles
Journal:  Appl Environ Microbiol       Date:  2012-09-21       Impact factor: 4.792

5.  Pyrogallol as a glutathione depletor induces apoptosis in HeLa cells.

Authors:  Yong Hwan Han; Sung Zoo Kim; Suhn Hee Kim; Woo Hyun Park
Journal:  Int J Mol Med       Date:  2008-06       Impact factor: 4.101

6.  Overexpression of PAD1 and FDC1 results in significant cinnamic acid decarboxylase activity in Saccharomyces cerevisiae.

Authors:  Peter Richard; Kaarina Viljanen; Merja Penttilä
Journal:  AMB Express       Date:  2015-02-18       Impact factor: 3.298

Review 7.  Metabolic engineering of microorganisms for production of aromatic compounds.

Authors:  Damla Huccetogullari; Zi Wei Luo; Sang Yup Lee
Journal:  Microb Cell Fact       Date:  2019-02-26       Impact factor: 5.328

8.  Engineering catechol 1, 2-dioxygenase by design for improving the performance of the cis, cis-muconic acid synthetic pathway in Escherichia coli.

Authors:  Li Han; Pi Liu; Jixue Sun; Yuanqing Wu; Yuanyuan Zhang; Wujiu Chen; Jianping Lin; Qinhong Wang; Yanhe Ma
Journal:  Sci Rep       Date:  2015-08-26       Impact factor: 4.379

9.  The complete genome of Blastobotrys (Arxula) adeninivorans LS3 - a yeast of biotechnological interest.

Authors:  Gotthard Kunze; Claude Gaillardin; Małgorzata Czernicka; Pascal Durrens; Tiphaine Martin; Erik Böer; Toni Gabaldón; Jose A Cruz; Emmanuel Talla; Christian Marck; André Goffeau; Valérie Barbe; Philippe Baret; Keith Baronian; Sebastian Beier; Claudine Bleykasten; Rüdiger Bode; Serge Casaregola; Laurence Despons; Cécile Fairhead; Martin Giersberg; Przemysław Piotr Gierski; Urs Hähnel; Anja Hartmann; Dagmara Jankowska; Claire Jubin; Paul Jung; Ingrid Lafontaine; Véronique Leh-Louis; Marc Lemaire; Marina Marcet-Houben; Martin Mascher; Guillaume Morel; Guy-Franck Richard; Jan Riechen; Christine Sacerdot; Anasua Sarkar; Guilhem Savel; Joseph Schacherer; David J Sherman; Nils Stein; Marie-Laure Straub; Agnès Thierry; Anke Trautwein-Schult; Benoit Vacherie; Eric Westhof; Sebastian Worch; Bernard Dujon; Jean-Luc Souciet; Patrick Wincker; Uwe Scholz; Cécile Neuvéglise
Journal:  Biotechnol Biofuels       Date:  2014-04-24       Impact factor: 6.040

10.  Metabolic Engineering of the Shikimate Pathway for Production of Aromatics and Derived Compounds-Present and Future Strain Construction Strategies.

Authors:  Nils J H Averesch; Jens O Krömer
Journal:  Front Bioeng Biotechnol       Date:  2018-03-26
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