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Article ; Online: Engineering 5-hydroxymethylfurfural (HMF) oxidation in Pseudomonas boosts tolerance and accelerates 2,5-furandicarboxylic acid (FDCA) production.

Lechtenberg, Thorsten / Wynands, Benedikt / Wierckx, Nick

2023 Volume 81, Page(s) 262–272

Abstract: Due to its tolerance properties, Pseudomonas has gained particular interest as host for oxidative upgrading of the toxic aldehyde 5-hydroxymethylfurfural (HMF) into 2,5-furandicarboxylic acid (FDCA), a promising biobased alternative to terephthalate in ... ...

Abstract	Due to its tolerance properties, Pseudomonas has gained particular interest as host for oxidative upgrading of the toxic aldehyde 5-hydroxymethylfurfural (HMF) into 2,5-furandicarboxylic acid (FDCA), a promising biobased alternative to terephthalate in polyesters. However, until now, the native enzymes responsible for aldehyde oxidation are unknown. Here, we report the identification of the primary HMF-converting enzymes of P. taiwanensis VLB120 and P. putida KT2440 by extended gene deletions. The key players in HMF oxidation are a molybdenum-dependent periplasmic oxidoreductase and a cytoplasmic dehydrogenase. Deletion of the corresponding genes almost completely abolished HMF oxidation, leading instead to aldehyde reduction. In this context, two HMF-reducing dehydrogenases were also revealed. These discoveries enabled enhancement of Pseudomonas' furanic aldehyde oxidation machinery by genomic overexpression of the respective genes. The resulting BOX strains (Boosted OXidation) represent superior hosts for biotechnological synthesis of FDCA from HMF. The increased oxidation rates provide greatly elevated HMF tolerance, thus tackling one of the major drawbacks of whole-cell catalysis with this aldehyde. Furthermore, the ROX (Reduced OXidation) and ROAR (Reduced Oxidation And Reduction) deletion mutants offer a solid foundation for future development of Pseudomonads as biotechnological chassis notably for scenarios where rapid HMF conversion is undesirable.
MeSH term(s)	Pseudomonas/genetics ; Furaldehyde ; Furans ; Dicarboxylic Acids
Chemical Substances	5-hydroxymethylfurfural (70ETD81LF0) ; 2,5-furandicarboxylic acid (73C4JJ695C) ; Furaldehyde (DJ1HGI319P) ; Furans ; Dicarboxylic Acids
Language	English
Publishing date	2023-12-26
Publishing country	Belgium
Document type	Journal Article
ZDB-ID	1470383-x
ISSN	1096-7184 ; 1096-7176
ISSN (online)	1096-7184
ISSN	1096-7176
DOI	10.1016/j.ymben.2023.12.010
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Book ; Online ; Thesis: Strain- and process engineering for polyketides production with Pseudomonas taiwanensis VLB120 in two-phase cultivations

Schwanemann, Tobias Philipp [Verfasser] / Wierckx, Nick [Gutachter] / Frunzke, Julia [Gutachter]

2024

Author's details	Tobias Philipp Schwanemann ; Gutachter: Nick Wierckx, Julia Frunzke
Keywords	Technische Chemie ; Technical Chemistry
Subject code	sg660
Language	English
Publisher	Universitäts- und Landesbibliothek der Heinrich-Heine-Universität Düsseldorf
Publishing place	Düsseldorf
Document type	Book ; Online ; Thesis
Database	Digital theses on the web

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Book ; Online ; Thesis: Enabling mixed microbial upcycling of plastic monomers

Ackermann, Yannic [Verfasser] / Wierckx, Nick [Gutachter] / Axmann, Ilka [Gutachter]

2024

Author's details	Yannic Sebastian Ackermann ; Gutachter: Nick Wierckx, Ilka Axmann
Keywords	Technische Chemie ; Technical Chemistry
Subject code	sg660
Language	English
Publisher	Universitäts- und Landesbibliothek der Heinrich-Heine-Universität Düsseldorf
Publishing place	Düsseldorf
Document type	Book ; Online ; Thesis
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Article: Editorial: Microbial Degradation of Plastics.

Wei, Ren / Wierckx, Nick

Frontiers in microbiology

2021 Volume 12, Page(s) 635621

Language	English
Publishing date	2021-02-11
Publishing country	Switzerland
Document type	Editorial
ZDB-ID	2587354-4
ISSN	1664-302X
ISSN	1664-302X
DOI	10.3389/fmicb.2021.635621
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Article ; Online: Microbial synthesis of the plant natural product precursor p-coumaric acid with Corynebacterium glutamicum.

Mutz, Mario / Kösters, Dominic / Wynands, Benedikt / Wierckx, Nick / Marienhagen, Jan

Microbial cell factories

2023 Volume 22, Issue 1, Page(s) 209

Abstract: Background: Phenylpropanoids such as p-coumaric acid represent important precursors for the synthesis of a broad range of plant secondary metabolites including stilbenoids, flavonoids, and lignans, which are of pharmacological interest due to their ... ...

Abstract	Background: Phenylpropanoids such as p-coumaric acid represent important precursors for the synthesis of a broad range of plant secondary metabolites including stilbenoids, flavonoids, and lignans, which are of pharmacological interest due to their health-promoting properties. Although extraction from plant material or chemical synthesis is possible, microbial synthesis of p-coumaric acid from glucose has the advantage of being less expensive and more resource efficient. In this study, Corynebacterium glutamicum was engineered for the production of the plant polyphenol precursor p-coumaric acid from glucose. Results: Heterologous expression of the tyrosine ammonia-lyase encoding gene from Flavobacterium johnsoniae enabled the conversion of endogenously provided tyrosine to p-coumaric acid. Product consumption was avoided by abolishing essential reactions of the phenylpropanoid degradation pathway. Accumulation of anthranilate as a major byproduct was eliminated by reducing the activity of anthranilate synthase through targeted mutagenesis to avoid tryptophan auxotrophy. Subsequently, the carbon flux into the shikimate pathway was increased, phenylalanine biosynthesis was reduced, and phosphoenolpyruvate availability was improved to boost p-coumaric acid accumulation. A maximum titer of 661 mg/L p-coumaric acid (4 mM) in defined mineral medium was reached. Finally, the production strain was utilized in co-cultivations with a C. glutamicum strain previously engineered for the conversion of p-coumaric acid into the polyphenol resveratrol. These co-cultivations enabled the synthesis of 31.2 mg/L (0.14 mM) resveratrol from glucose without any p-coumaric acid supplementation. Conclusions: The utilization of a heterologous tyrosine ammonia-lyase in combination with optimization of the shikimate pathway enabled the efficient production of p-coumaric acid with C. glutamicum. Reducing the carbon flux into the phenylalanine and tryptophan branches was the key to success along with the introduction of feedback-resistant enzyme variants.
MeSH term(s)	Resveratrol/metabolism ; Corynebacterium glutamicum/genetics ; Corynebacterium glutamicum/metabolism ; Tryptophan/metabolism ; Plants/genetics ; Glucose/metabolism ; Polyphenols ; Phenylalanine/metabolism ; Metabolic Engineering
Chemical Substances	Resveratrol (Q369O8926L) ; p-coumaric acid (IBS9D1EU3J) ; Tryptophan (8DUH1N11BX) ; shikimate ; Glucose (IY9XDZ35W2) ; Polyphenols ; Phenylalanine (47E5O17Y3R)
Language	English
Publishing date	2023-10-13
Publishing country	England
Document type	Journal Article
ZDB-ID	2091377-1
ISSN	1475-2859 ; 1475-2859
ISSN (online)	1475-2859
ISSN	1475-2859
DOI	10.1186/s12934-023-02222-y
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Article ; Online: A Pseudomonas taiwanensis malonyl-CoA platform strain for polyketide synthesis.

Schwanemann, Tobias / Otto, Maike / Wynands, Benedikt / Marienhagen, Jan / Wierckx, Nick

Metabolic engineering

2023 Volume 77, Page(s) 219–230

Abstract: Malonyl-CoA is a central precursor for biosynthesis of a wide range of complex secondary metabolites. The development of platform strains with increased malonyl-CoA supply can contribute to the efficient production of secondary metabolites, especially if ...

Abstract	Malonyl-CoA is a central precursor for biosynthesis of a wide range of complex secondary metabolites. The development of platform strains with increased malonyl-CoA supply can contribute to the efficient production of secondary metabolites, especially if such strains exhibit high tolerance towards these chemicals. In this study, Pseudomonas taiwanensis VLB120 was engineered for increased malonyl-CoA availability to produce bacterial and plant-derived polyketides. A multi-target metabolic engineering strategy focusing on decreasing the malonyl-CoA drain and increasing malonyl-CoA precursor availability, led to an increased production of various malonyl-CoA-derived products, including pinosylvin, resveratrol and flaviolin. The production of flaviolin, a molecule deriving from five malonyl-CoA molecules, was doubled compared to the parental strain by this malonyl-CoA increasing strategy. Additionally, the engineered platform strain enabled production of up to 84 mg L
MeSH term(s)	Fatty Acids/metabolism ; Malonyl Coenzyme A/metabolism ; Polyketides/metabolism ; Pseudomonas/classification ; Pseudomonas/genetics ; Pseudomonas/metabolism ; Resveratrol/metabolism ; Secondary Metabolism ; Stilbenes/metabolism ; Coumaric Acids/metabolism ; Phenylalanine/metabolism ; Genome, Bacterial/genetics ; Sequence Deletion ; Acetyl Coenzyme A/metabolism ; Citrate (si)-Synthase/metabolism ; Pyruvic Acid/metabolism ; Phytoalexins/metabolism ; Naphthoquinones/metabolism
Chemical Substances	Fatty Acids ; flaviolin (479-05-0) ; Malonyl Coenzyme A (524-14-1) ; pinosylvin (881R434AIB) ; Polyketides ; Resveratrol (Q369O8926L) ; Stilbenes ; Coumaric Acids ; Phenylalanine (47E5O17Y3R) ; Acetyl Coenzyme A (72-89-9) ; Citrate (si)-Synthase (EC 2.3.3.1) ; Pyruvic Acid (8558G7RUTR) ; Phytoalexins ; Naphthoquinones
Language	English
Publishing date	2023-04-08
Publishing country	Belgium
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1470383-x
ISSN	1096-7184 ; 1096-7176
ISSN (online)	1096-7184
ISSN	1096-7176
DOI	10.1016/j.ymben.2023.04.001
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Book ; Online ; Thesis: Electrochemical pH-swing extraction for carboxylic acid purification

Gausmann, Marcel [Verfasser] / Jupke, Andreas [Akademischer Betreuer] / Wierckx, Nick [Akademischer Betreuer]

2024

Author's details	Marcel Gausmann ; Andreas Jupke, Nick Wierckx
Keywords	Technische Chemie ; Technical Chemistry
Subject code	sg660
Language	English
Publisher	Universitätsbibliothek der RWTH Aachen
Publishing place	Aachen
Document type	Book ; Online ; Thesis
Database	Digital theses on the web

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Article ; Online: Engineering a Pseudomonas taiwanensis 4-coumarate platform for production of para-hydroxy aromatics with high yield and specificity

Wynands, Benedikt / Kofler, Franziska / Sieberichs, Anka / da Silva, Nadine / Wierckx, Nick

Metabolic Engineering. 2023 July, v. 78 p.115-127

2023

Abstract: Aromatics are valuable bulk or fine chemicals with a myriad of important applications. Currently, their vast majority is produced from petroleum associated with many negative aspects. The bio-based synthesis of aromatics contributes to the much-required ... ...

Abstract	Aromatics are valuable bulk or fine chemicals with a myriad of important applications. Currently, their vast majority is produced from petroleum associated with many negative aspects. The bio-based synthesis of aromatics contributes to the much-required shift towards a sustainable economy. To this end, microbial whole-cell catalysis is a promising strategy allowing the valorization of abundant feedstocks derived from biomass to yield de novo-synthesized aromatics. Here, we engineered tyrosine-overproducing derivatives of the streamlined chassis strain Pseudomonas taiwanensis GRC3 for efficient and specific production of 4-coumarate and derived aromatics. This required pathway optimization to avoid the accumulation of tyrosine or trans-cinnamate as byproducts. Although application of tyrosine-specific ammonia-lyases prevented the formation of trans-cinnamate, they did not completely convert tyrosine to 4-coumarate, thereby displaying a significant bottleneck. The use of a fast but unspecific phenylalanine/tyrosine ammonia-lyase from Rhodosporidium toruloides (RtPAL) alleviated this bottleneck, but caused phenylalanine conversion to trans-cinnamate. This byproduct formation was greatly reduced through the reverse engineering of a point mutation in prephenate dehydratase domain-encoding pheA. This upstream pathway engineering enabled efficient 4-coumarate production with a specificity of >95% despite using an unspecific ammonia-lyase, without creating an auxotrophy. In shake flask batch cultivations, 4-coumarate yields of up to 21.5% (Cmol/Cmol) from glucose and 32.4% (Cmol/Cmol) from glycerol were achieved. Additionally, the product spectrum was diversified by extending the 4-coumarate biosynthetic pathway to enable the production of 4-vinylphenol, 4-hydroxyphenylacetate, and 4-hydroxybenzoate with yields of 32.0, 23.0, and 34.8% (Cmol/Cmol) from glycerol, respectively.
Keywords	4-hydroxybenzoic acid ; Pseudomonas ; Rhodosporidium toruloides ; biochemical pathways ; biomass ; byproducts ; catalytic activity ; culture flasks ; feedstocks ; glucose ; glycerol ; petroleum ; phenylalanine ; point mutation ; tyrosine ; tyrosine ammonia-lyase ; Aromatics ; Biocatalysis ; 4-Coumarate ; Metabolic engineering ; Phenylalanine/tyrosine ammonia-lyase
Language	English
Dates of publication	2023-07
Size	p. 115-127.
Publishing place	Elsevier Inc.
Document type	Article ; Online
ZDB-ID	1470383-x
ISSN	1096-7184 ; 1096-7176
ISSN (online)	1096-7184
ISSN	1096-7176
DOI	10.1016/j.ymben.2023.05.004
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: A Pseudomonas taiwanensis malonyl-CoA platform strain for polyketide synthesis

Schwanemann, Tobias / Otto, Maike / Wynands, Benedikt / Marienhagen, Jan / Wierckx, Nick

International Metabolic Engineering Society Metabolic Engineering. 2023 May, v. 77 p.219-230

2023

Abstract	Malonyl-CoA is a central precursor for biosynthesis of a wide range of complex secondary metabolites. The development of platform strains with increased malonyl-CoA supply can contribute to the efficient production of secondary metabolites, especially if such strains exhibit high tolerance towards these chemicals. In this study, Pseudomonas taiwanensis VLB120 was engineered for increased malonyl-CoA availability to produce bacterial and plant-derived polyketides. A multi-target metabolic engineering strategy focusing on decreasing the malonyl-CoA drain and increasing malonyl-CoA precursor availability, led to an increased production of various malonyl-CoA-derived products, including pinosylvin, resveratrol and flaviolin. The production of flaviolin, a molecule deriving from five malonyl-CoA molecules, was doubled compared to the parental strain by this malonyl-CoA increasing strategy. Additionally, the engineered platform strain enabled production of up to 84 mg L⁻¹ resveratrol from supplemented p-coumarate. One key finding of this study was that acetyl-CoA carboxylase overexpression majorly contributed to an increased malonyl-CoA availability for polyketide production in dependence on the used strain-background and whether downstream fatty acid synthesis was impaired, reflecting its complexity in metabolism. Hence, malonyl-CoA availability is primarily determined by competition of the production pathway with downstream fatty acid synthesis, while supply reactions are of secondary importance for compounds that derive directly from malonyl-CoA in Pseudomonas.
Keywords	Pseudomonas ; acetyl-CoA carboxylase ; biosynthesis ; fatty acids ; malonyl coenzyme A ; resveratrol ; secondary metabolites ; Polyketide ; Malonyl-CoA ; Stilbene ; Flaviolin ; Fatty acid biosynthesis
Language	English
Dates of publication	2023-05
Size	p. 219-230.
Publishing place	Elsevier Inc.
Document type	Article ; Online
Note	Pre-press version
ZDB-ID	1470383-x
ISSN	1096-7184 ; 1096-7176
ISSN (online)	1096-7184
ISSN	1096-7176
DOI	10.1016/j.ymben.2023.04.001
Database	NAL-Catalogue (AGRICOLA)

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Zs.A 6288: Show issues

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Article ; Online: Engineering a Pseudomonas taiwanensis 4-coumarate platform for production of para-hydroxy aromatics with high yield and specificity.

Wynands, Benedikt / Kofler, Franziska / Sieberichs, Anka / da Silva, Nadine / Wierckx, Nick

Metabolic engineering

2023 Volume 78, Page(s) 115–127

Abstract	Aromatics are valuable bulk or fine chemicals with a myriad of important applications. Currently, their vast majority is produced from petroleum associated with many negative aspects. The bio-based synthesis of aromatics contributes to the much-required shift towards a sustainable economy. To this end, microbial whole-cell catalysis is a promising strategy allowing the valorization of abundant feedstocks derived from biomass to yield de novo-synthesized aromatics. Here, we engineered tyrosine-overproducing derivatives of the streamlined chassis strain Pseudomonas taiwanensis GRC3 for efficient and specific production of 4-coumarate and derived aromatics. This required pathway optimization to avoid the accumulation of tyrosine or trans-cinnamate as byproducts. Although application of tyrosine-specific ammonia-lyases prevented the formation of trans-cinnamate, they did not completely convert tyrosine to 4-coumarate, thereby displaying a significant bottleneck. The use of a fast but unspecific phenylalanine/tyrosine ammonia-lyase from Rhodosporidium toruloides (RtPAL) alleviated this bottleneck, but caused phenylalanine conversion to trans-cinnamate. This byproduct formation was greatly reduced through the reverse engineering of a point mutation in prephenate dehydratase domain-encoding pheA. This upstream pathway engineering enabled efficient 4-coumarate production with a specificity of >95% despite using an unspecific ammonia-lyase, without creating an auxotrophy. In shake flask batch cultivations, 4-coumarate yields of up to 21.5% (Cmol/Cmol) from glucose and 32.4% (Cmol/Cmol) from glycerol were achieved. Additionally, the product spectrum was diversified by extending the 4-coumarate biosynthetic pathway to enable the production of 4-vinylphenol, 4-hydroxyphenylacetate, and 4-hydroxybenzoate with yields of 32.0, 23.0, and 34.8% (Cmol/Cmol) from glycerol, respectively.
MeSH term(s)	Glycerol ; Cinnamates/metabolism ; Tyrosine/genetics ; Tyrosine/metabolism ; Phenylalanine ; Metabolic Engineering
Chemical Substances	Glycerol (PDC6A3C0OX) ; Cinnamates ; Tyrosine (42HK56048U) ; Phenylalanine (47E5O17Y3R)
Language	English
Publishing date	2023-05-18
Publishing country	Belgium
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1470383-x
ISSN	1096-7184 ; 1096-7176
ISSN (online)	1096-7184
ISSN	1096-7176
DOI	10.1016/j.ymben.2023.05.004
Database	MEDical Literature Analysis and Retrieval System OnLINE

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