A quinone mediator drives oxidations catalysed by alcohol dehydrogenase-containing cell lysates

Haas, Julian; Schätzle, Michael A.; Husain, Syed Masood; Schulz-Fincke, Johannes; Jung, Manfred; Hummel, Werner; Müller, Michael; Lüdeke, Steffen

doi:10.1039/c5cc10316a

Cited by 14 publications

(11 citation statements)

References 20 publications

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“…For this purpose, NAD(P)H‐dependent NfsB (oxygen‐insensitive nitroreductase) of Escherichia coli strain K‐12 was used . NfsB has previously been applied to NADP + regeneration by using the concept of redox cycling for the oxidation of alcohols to ketones by alcohol dehydrogenase . Therefore, the synthesized NfsB gene was cloned into the pET19b vector and expressed in E. coli strain BL21.…”

Section: Resultsmentioning

confidence: 99%

A Redox‐Based Superoxide Generation System Using Quinone/Quinone Reductase

Singh

Husain

2018

ChemBioChem

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Superoxide (O ) generation in biological systems is achieved through some of the most complex enzymatic systems. Of these, only xanthine/xanthine oxidase has been used for in vitro biochemical studies. However, it suffers from limitations such as a lack of suitable heterologous expression system for xanthine oxidase and the irreversible consumption and low solubility of xanthine under physiological conditions. Herein, we report a redox-based, enzyme-catalyzed system, in which autoxidation of hydroquinone to quinone via semiquinone results in superoxide generation. Quinone is reduced back to hydroquinone by using the NfsB (oxygen-insensitive nitroreductase) enzyme of Escherichia coli strain K-12 and nicotinamide adenine dinucleotide phosphate hydride (NADPH; which is regenerated by using the glucose/glucose dehydrogenase system). This new system relies on quinones that can be recycled and have superior water solubility, as well as enzymes that are heterologously expressed. By using a variety of quinones and reaction conditions, along with a comparison of real-time fluorescence, menadione has been identified as the optimal substrate for superoxide generation. The new redox-based system presents a viable alternative for studying the biochemistry of superoxide under different physiological and pathological conditions.

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Section: Resultsmentioning

confidence: 99%

A Redox‐Based Superoxide Generation System Using Quinone/Quinone Reductase

Singh

Husain

2018

ChemBioChem

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“…Spontaneous autoxidation of 32 by molecular oxygen from ambient air (see Scheme 7) suggested that quinones, due to their redox properties, may interfere with enzymes involved in maintaining the NAD(P) + /NAD(P)H ratio both in eukaryotic and prokaryotic cells. 54 This led us to apply spontaneous reoxidation of the hydroquinones formed by cellular NAD(P)H-dependent quinone reductases as a source of continuous supply of NAD(P) + . The redox system of lawsone ( 30) and E. coli cell lysate was successfully utilized to oxidize primary and secondary alcohols to the corresponding carbonyl compounds by an NAD(P) + -dependent alcohol dehydrogenase (ADH) (Scheme 12).…”

Section: Nadp + Regeneration Using Lawsone As Mediatormentioning

confidence: 99%

Fungal Dihydroxynaphthalene-Melanin: Diversity-Oriented Biosynthesis through Enzymatic and Non-enzymatic Transformations

Husain

Müller

2017

Synlett

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Tetrahydroxynaphthalene reductase (T4HNR) from Magnaporthe grisea catalyzes the reduction of polyhydroxynaphthalenes, hydroxynaphthoquinones, and 1,4-diketones, with extensive ramifications for the biosynthesis of (shunt) metabolites related to 1,8-dihydroxynaphthalene (DHN)-melanin biosynthesis. Hence, an extended model for DHN-melanin biosynthesis has been developed which is based on a screening hypothesis involving non-enzymatic transformations such as oxidations and tautomerism. This has led to the broadening of the functions of several short-chain dehydrogenases/reductases (SDRs) capable of reducing polyhydroxyanthracenes, polyhydroxynaphthalenes, and polyhydroxybenzenes. Our work, broadening the scope of enzymatic dearomatization reactions, provides access to the biocatalytic synthesis of a variety of natural and natural-like products. Furthermore, the results described in this account provide the basis for the identification of other SDRs amenable to reducing aromatic compounds, and thus enable the identification of biosynthetic gene clusters most likely involved in the biosynthesis of aromatic polyketides.1 Introduction2 Biosynthesis of 1,8-Dihydroxynaphthalene (DHN)3 Biosynthesis of Shunt Metabolites and the Origin of Molecular Diversity3.1 Role of Spontaneous Non-enzymatic Oxidations3.2 Role of T4HNR and T3HNR3.3 Role of Tautomerism in the Biosynthesis of (Shunt) Metabolites4 Extended Melanin Biosynthesis: A Screening Hypothesis5 Useful Outcomes of the Newly Identified Melanin Biosynthetic Pathway5.1 NADP+ Regeneration Using Lawsone as Mediator5.2 Anthrahydroquinone as an Intermediate in the Biosynthesis of Chrysophanol and Other Anthraquinone-Derived Products5.3 Combination of T3HNR and GDH To Access trans-Ketodiols5.4 Phloroglucinol Reductases (PGRs) To Dearomatize Monomeric Phenols6 Conclusion

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“…Recently, its bactericidal, fungicidal, antimalarial and cytostatic properties were reported 3–5 . More importantly, its role as a redox mediator was elucidated in many works 6, 7 . As a result, its application field was greatly extended to the pharmaceutical, chemical and other industries 8–11 .…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of 2-hydroxyl-1,4 naphthoquinone (lawsone) by Pseudomonas taiwanensis LH-3 isolated from activated sludge

Cai

Ding

et al. 2017

Sci Rep

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2-hydroxy-1,4 naphthoquinone (lawsone) is widely used and induces environmental pollutions during its production and application. In the present study, a lawsone-degrading bacterium strain, LH-3 was successfully isolated from the activated sludge. Based on the 16S rRNA gene analysis, the strain LH-3 phylogenetically belonged to the Pseudomonas taiwanensis. It could degrade 200 mg L−1 lawsone completely in 9 h with an inoculum quantity of 1% (v/v). The effects of environmental conditions on the degradation process and the degradation pathway were systematically investigated. LH-3 could maintain its high degradation efficiency under high salt condition. The identified intermediates of salicylic acid, 2-hydroxy-4-oxo-chroman-2-carboxylic acid, and catechol elucidated the potential degradation pathway. Furthermore, the immobilized LH-3 strain cells prepared with alginate gel and biochar performed excellent stability in nine successive degradation runs. It could sucessfully survive in laboratory scale sequencing batch reactor and become to be the dominant species. This study clearly revealed that LH-3 could serve as an attractive candidate for the microbial remediation of lawsone-containing wastewater.

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A quinone mediator drives oxidations catalysed by alcohol dehydrogenase-containing cell lysates

Cited by 14 publications

References 20 publications

A Redox‐Based Superoxide Generation System Using Quinone/Quinone Reductase

A Redox‐Based Superoxide Generation System Using Quinone/Quinone Reductase

Fungal Dihydroxynaphthalene-Melanin: Diversity-Oriented Biosynthesis through Enzymatic and Non-enzymatic Transformations

Biodegradation of 2-hydroxyl-1,4 naphthoquinone (lawsone) by Pseudomonas taiwanensis LH-3 isolated from activated sludge

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