Enzyme cascade reactions: synthesis of furandicarboxylic acid (FDCA) and carboxylic acids using oxidases in tandem

McKenna, Shane; Leimkühler, Silke; Herter, Susanne; Turner, Nicholas J.; Carnell, Andrew J.

doi:10.1039/c5gc00707k

Cited by 134 publications

(130 citation statements)

References 42 publications

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“…A bacterial flavoprotein oxidase was shown to be capable of performing the complete oxidation of HMF into FDCA [8,9]. Similar results were obtained by using a combination of two or more enzymes [10,11].…”

Section: Introductionsupporting

confidence: 71%

Conversion of Furans by Baeyer-Villiger Monooxygenases

Kumar

Fraaije

2017

Catalysts

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Various furans are considered as valuable platform chemicals as they can be derived from plant biomass. Yet, for their exploitation, follow-up chemistry is required. Here we demonstrate that Baeyer-Villiger monooxygenases (BVMOs) can be used as biocatalysts for the selective oxidation of several furans, including 5-(hydroxymethyl) furfural (HMF) and furfural. A total of 15 different BVMOs were tested for their activity on furfural, which revealed that most of the biocatalysts were active on this aromatic aldehyde. Phenylacetone monooxygenase (PAMO) and a mutant thereof (PAMO M446G ) were selected for studying their biocatalytic potential in converting furfural and some other furans. While BVMOs are usually known to form an ester or lactone as a 'normal' product by inserting an oxygen atom adjacent to the carbonyl carbon of the substrate, our results reveal that both biocatalysts produce furanoid acids as the main product from the corresponding aldehydes. Altogether, our study shows that BVMOs can be employed for the selective oxidation of furans.

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Section: Introductionsupporting

confidence: 71%

Conversion of Furans by Baeyer-Villiger Monooxygenases

Kumar

Fraaije

2017

Catalysts

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“…There are many examples of the successful utilisation of rational and directed methods of protein engineering for the creation of enzymes with increased suitability for industrial applications . They not only include tailoring of single enzymes but also the application of multiple enzymes to facilitate the single‐step synthesis of compounds with more complex architectures and numerous functional groups . These concurrent enzymatic transformations offer advantages in the form of reduced reaction times and lower costs …”

Section: Evolution Of Enzymes Suitable For Industrial Applicationsmentioning

confidence: 58%

Directed Evolution of Enzymes for Industrial Biocatalysis

2015

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Enzymes have the potential to catalyse a wide variety of chemical reactions. They are increasingly being sought as environmentally friendly and cost-effective alternatives to conventional catalysts used in industries ranging from bioremediation to applications in medicine and pharmaceutics. Despite the benefits, they are not without their limitations. Many naturally occurring enzymes are not suitable for use outside of their native cellular environments. However, protein engineering can be used to generate enzymes tailored for specific industrial applications. Directed evolution is particularly useful and can be employed even when lack of structural information impedes the use of rational design. The aim of this review is to provide an overview of current industrial applications of enzyme technology and to show how directed evolution can be used to modify and to enhance enzyme properties. This includes a brief discussion on library generation and a more detailed focus on library screening methods, which are critical to any directed evolution experiment.

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“…58 Nesse estudo, primeiramente a galactose oxidase M 3-5 leva a formação do dialdeído a partir do 5-HMF que, em seguida, sofre uma reação de oxidação por intermédio da enzima aldeído oxidase PaoABC conduzindo ao produto desejado com 74% de rendimento isolado (Esquema 7). Esquema 7.…”

Section: Esquema 4 Subprodutos Formados Na Reação De Desidratação Daunclassified

Production of 5-(Hydroxymethyl)furfural from Biomass: Synthetic Challenges and Applications as Building Block in Polymers and Liquid Fuel Production

Pastre

2017

Rev. Virtual Quim.

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Abstract:The production of compounds known as building blocks from renewable resources has aroused much interest from the scientific community in the recent years. Building blocks are molecules that exhibit in most cases multiple functional groups and offer unique possibilities to be chemically or biologically transformed into high added-value compounds. Some examples of these include biopolymers, biofuels, solvents, and biochemicals. Among the examples of building blocks, 5-(hydroxymethyl)furfural (5-HMF) is presented as one of the most studied compound in recent years due to its potential as raw material for preparation of bio-based chemicals. In this context, in the proposed review, the recent synthetic methodologies for 5-HMF production from renewable resources will be presented, as well as the application of 5-HMF as raw material for liquid biofuels and biopolymers production.Keywords: 5-(Hydroxymethyl)furfural; Bio-polymers; Bio-fuels; Green chemistry. ResumoA produção de compostos conhecidos como blocos de construção a partir de recursos renováveis tem despertado muito interesse da comunidade científica nos últimos anos. Blocos de construção são moléculas que apresentam, na grande maioria das vezes, múltiplos grupos funcionais e oferecem excelentes oportunidades para serem quimicamente ou biologicamente transformadas em compostos com alto valor agregado. Alguns exemplos de compostos com alto valor agregado incluem bio-polímeros, bio-combustíveis, bio-solventes e os compostos de química de base. Entre os exemplos que podemos citar como blocos construtores, o 5-(hidroximetil)furfural (5-HMF) apresenta-se como um dos mais estudados nos últimos anos devido ao seu potencial como matéria-prima para preparação de insumos químicos. Nesse contexto, este artigo de revisão tem por objetivo apresentar as recentes metodologias sintéticas para preparação de 5-HMF a partir de recursos renováveis, bem como a aplicação de 5-HMF na produção de biocombustíveis líquidos e biopolímeros.

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Enzyme cascade reactions: synthesis of furandicarboxylic acid (FDCA) and carboxylic acids using oxidases in tandem

Abstract: Three enzymes are combined under mild conditions for the preparative scale oxidation of HMF to FDCA and a range of 10 alcohols.

Cited by 134 publications

References 42 publications

Conversion of Furans by Baeyer-Villiger Monooxygenases

Conversion of Furans by Baeyer-Villiger Monooxygenases

Directed Evolution of Enzymes for Industrial Biocatalysis

Production of 5-(Hydroxymethyl)furfural from Biomass: Synthetic Challenges and Applications as Building Block in Polymers and Liquid Fuel Production

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