Alcohol Dehydrogenases as Catalysts in Organic Synthesis

Miranda, Amanda Silva de; Milagre, Cíntia D. F.; Hollmann, Frank

doi:10.3389/fctls.2022.900554

Cited by 33 publications

(26 citation statements)

References 330 publications

(346 reference statements)

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“…2-HPP is an essential intermediate in the stereoselective synthesis of diols. For instance, 1-phenylpropane-1,2-diol (PPD), an important agent and versatile building block in pharmaceutical industry, can be obtained by subsequent oxidoreduction of 2-HPP using alcohol dehydrogenase [ 5 , 6 ]. Different α-hydroxy ketone derivatives can be formed by numerous chemical synthetic routes [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Optimized enantioselective (S)-2-hydroxypropiophenone synthesis by free- and encapsulated-resting cells of Pseudomonas putida

et al. 2023

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Background Aromatic α-hydroxy ketones, such as S-2-hydroxypropiophenone (2-HPP), are highly valuable chiral building blocks useful for the synthesis of various pharmaceuticals and natural products. In the present study, enantioselective synthesis of 2-HPP was investigated by free and immobilized whole cells of Pseudomonas putida ATCC 12633 starting from readily-available aldehyde substrates. Whole resting cells of P. putida, previously grown in a culture medium containing ammonium mandelate, are a source of native benzoylformate decarboxylase (BFD) activity. BFD produced by induced P. putida resting cells is a highly active biocatalyst without any further treatment in comparison with partially purified enzyme preparations. These cells can convert benzaldehyde and acetaldehyde into the acyloin compound 2-HPP by BFD-catalyzed enantioselective cross-coupling reaction. Results The reaction was carried out in the presence of exogenous benzaldehyde (20 mM) and acetaldehyde (600 mM) as substrates in 6 mL of 200 mM phosphate buffer (pH 7) for 3 h. The optimal biomass concentration was assessed to be 0.006 g dry cell weight (DCW) mL− 1. 2-HPP titer, yield and productivity using the free cells were 1.2 g L− 1, 0.56 g 2-HPP/g benzaldehyde (0.4 mol 2-HPP/mol benzaldehyde), 0.067 g 2-HPP g− 1 DCW h− 1, respectively, under optimized biotransformation conditions (30 °C, 200 rpm). Calcium alginate (CA)–polyvinyl alcohol (PVA)-boric acid (BA)-beads were used for cell entrapment. Encapsulated whole-cells were successfully employed in four consecutive cycles for 2-HPP production under aerobic conditions without any noticeable beads degradation. Moreover, there was no production of benzyl alcohol as an unwanted by-product. Conclusions Bioconversion by whole P. putida resting cells is an efficient strategy for the production of 2-HPP and other α-hydroxyketones. Graphical abstract

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Section: Introductionmentioning

confidence: 99%

Optimized enantioselective (S)-2-hydroxypropiophenone synthesis by free- and encapsulated-resting cells of Pseudomonas putida

et al. 2023

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“…For the transformation of benzylic alcohols into the desired benzaldehyde derivates, a range of biocatalytic methods have been reported (Scheme 1). Alcohol dehydrogenases, for example, catalyse the NAD(P) + -dependent oxidation of benzyl alcohols (Scheme 1A) [8]. Their nicotinamide cofactor-dependency, however, challenges the economic feasibility of these reactions and necessitates further efforts to ensure catalytic use of NAD(P) + and in situ regeneration.…”

Section: Introductionmentioning

confidence: 99%

Bienzymatic Cascade Combining a Peroxygenase with an Oxidase for the Synthesis of Aromatic Aldehydes from Benzyl Alcohols

Li²,

Zhang³

et al. 2023

Catalysts

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Aromatic aldehydes are important aromatic compounds for the flavour and fragrance industry. In this study, a parallel cascade combining aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) and unspecific peroxygenase from the basidiomycete Agrocybe aegerita (AaeUPO) to convert aromatic primary alcohols into high-value aromatic aldehydes is proposed. Key influencing factors in the process of enzyme cascade catalysis, such as enzyme dosage, pH and temperature, were investigated. The universality of PeAAOx coupled with AaeUPO cascade catalysis for the synthesis of aromatic aldehyde flavour compounds from aromatic primary alcohols was evaluated. In a partially optimised system (comprising 30 μM PeAAOx, 2 μM AaeUPO at pH 7 and 40 °C) up to 84% conversion of 50 mM veratryl alcohol into veratryl aldehyde was achieved in a self-sufficient aerobic reaction. Promising turnover numbers of 2800 and 21,000 for PeAAOx and AaeUPO, respectively, point towards practical applicability.

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“…Redox enzymes (or oxidoreductases) that play a key role in biological energy transduction can be used to catalyze various synthetically useful redox reactions, − such as asymmetric reduction of carbonyl groups, oxygenation of C–H bonds, epoxidation of CC bonds, and Baeyer–Villiger oxidation. − These redox reactions can be applied in the synthesis of pharmaceuticals, food additives, and fuels . For example, the oxidation of alcohol is a crucial reaction in organic synthesis, and alcohol dehydrogenase can carry out highly selective conversions of primary alcohols to either aldehydes or acids. − However, over 80% of oxidoreductases in nature are dependent on nicotinamide cofactors reduced nicotinamide adenine dinucleotide (NADH)/β-nicotinamide adenine dinucleotide (NAD + ) or reduced nicotinamide adenine dinucleotide phosphate (NADPH)/β-nicotinamide adenine dinucleotide phosphate (NADP + ) for their catalytic activities. Nature has developed complicated electron transport chains to regenerate the required cofactor species, while the mimic of these natural processes is extremely challenging for synthetic systems.…”

Section: Introductionmentioning

confidence: 99%

AIE Polymer Micelle/Vesicle Photocatalysts Combined with Native Enzymes for Aerobic Photobiocatalysis

Zhang

Chen

2022

J. Am. Chem. Soc.

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Biocatalytic transformation has attracted increasing attention in the green synthesis of chemicals due to the diversity of enzymes, their high catalytic activities and specificities, and environmentally benign conditions. Most redox enzymes in nature are dependent on nicotinamide cofactors like β-nicotinamide adenine dinucleotide (NAD + )/reduced nicotinamide adenine dinucleotide (NADH). The use of solar energy, especially visible light, in the regeneration of cofactors through the combination of photocatalysis and biocatalysis provides an extraordinary opportunity to make complete green processes. However, the combination of photocatalysts and enzymes has been challenged by the rapid degradation and deactivation of the enzymatic material by photogenerated reactive oxygen species (ROS). Here, we design core−shell structured polymer micelles and vesicles with aggregation-induced emission (AIE) as visible-light-mediated photocatalysts for highly stable and recyclable photobiocatalysis under aerobic conditions. NAD + from NADH can be efficiently regenerated by the photoactive hydrophobic core of polymer micelles and the hydrophobic membrane of polymer vesicles, while the enzymatic material (glucose 1dehydrogenase) is screened from the attack of photogenerated ROS by the hydrophilic surface layer of polymer colloids. After at least 10 regeneration cycles, the enzyme keeps its active state; meanwhile, polymer micelles and vesicles maintain their photocatalytic activity. These polymer colloids show the potential to be developed for the implementation of industrially relevant photobiocatalytic systems.

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Alcohol Dehydrogenases as Catalysts in Organic Synthesis

Cited by 33 publications

References 330 publications

Optimized enantioselective (S)-2-hydroxypropiophenone synthesis by free- and encapsulated-resting cells of Pseudomonas putida

Optimized enantioselective (S)-2-hydroxypropiophenone synthesis by free- and encapsulated-resting cells of Pseudomonas putida

Bienzymatic Cascade Combining a Peroxygenase with an Oxidase for the Synthesis of Aromatic Aldehydes from Benzyl Alcohols

AIE Polymer Micelle/Vesicle Photocatalysts Combined with Native Enzymes for Aerobic Photobiocatalysis

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