Biotechnological production of vanillin using immobilized enzymes

Furuya, Toshiki; Kuroiwa, Mari; Kino, Kuniki

doi:10.1016/j.jbiotec.2016.12.021

Cited by 81 publications

(57 citation statements)

References 24 publications

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“…[85] In order to minimize chemical waste and avoid non-sustainable synthetic methodologies, the scientific 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 community is moving towards the use of biomass as feedstock for vanillin production, through catalyzed oxidation strategies employing green oxidants such as H 2 O 2 and molecular oxygen ( Figure 7). [86][87][88][89] Lactic acid, another commodity chemical obtained from biomass resources, [90] offers new possibilities for synthesis of chemical due to its functionalitys, namely hydroxyl and carboxylic acid functions [91,92] Such molecule can give rise to several add-value compounds such as acetaldehyde by decarbonylation/decarboxylation, 2,3-pentanedione by condensation, acrylic acid by dehydration, pyruvic acid by dehydrogenation, propanoic acid or 1,2-propanediol by reduction, ethyl lactate by esterification and poly-lactic acid by polymerization. [93] The proper choice of the catalytic system results to be a crucial factor for the selective formation of the desired product.…”

Section: Catalyst Preparation Methodologiesmentioning

confidence: 99%

“…[77] Copyright, 2015 Royal Society of Chemistry. [87] Copyright, 2018 Frontiers and (B) Proline-based heterogeneous organocatalyst for selective production of vanillin from vanillyl alcohol and isoeugenol. Reproduced with permission of ref.…”

Section: Catalyst Preparation Methodologiesmentioning

confidence: 99%

“…Other preeminent molecules derived from lignin such as eugenol, isoeugenol, and ferulic acid have been employed for the synthesis of vanillin via oxidation pathways. Synthetic vanillin, currently produced from petro‐based intermediates (glyoxylic acid and guaiacol), possesses a remarkable value as flavoring agent in cosmetic, pharmaceutical, food and fine chemical industries . In order to minimize chemical waste and avoid non‐sustainable synthetic methodologies, the scientific community is moving towards the use of biomass as feedstock for vanillin production, through catalyzed oxidation strategies employing green oxidants such as H 2 O 2 and molecular oxygen (Figure ) …”

Section: Catalysismentioning

confidence: 99%

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Environmental Catalysis: Present and Future

et al. 2018

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Environmental catalysis plays a crucial role in sustainable development by the design of novel catalytic materials and technologies. Several environmental issues are addressed by catalytic processes such as decomposition of pollutants for air, water and soil remediation, hydrogen production, CO2 reduction and biomass valorization, just to name a few. This contribution aims to provide a general overview of the main concepts and current advances in the environmental catalysis field. Special attention has been paid to photocatalysis and electrocatalysis, as sub‐areas of catalysis with tremendous potential in sustainable applications, in particular with regard to the promotion of sustainable energies. In this contribution, the partnership between Catalysis and Green Chemistry is presented, in a comprehensive way, as an open research line which is imperative and decisive for a more sustainable future.

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Section: Catalyst Preparation Methodologiesmentioning

confidence: 99%

Section: Catalyst Preparation Methodologiesmentioning

confidence: 99%

Section: Catalysismentioning

confidence: 99%

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Environmental Catalysis: Present and Future

et al. 2018

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“…Two coenzyme‐independent enzymes, namely the decarboxylase Fdc (ferulic acid decarboxylase Fdc from Bacillus pumilus ) and the oxygenase Cso2 (4‐vinylguaiacol oxygenase Cso2 from Caulobacter segnis ), were immobilized on Sepabeads EC‐EA anion‐exchange carrier and used for the synthesis of vanillin via a simultaneous two‐step cascade starting from ferulic acid (Scheme ) . The immobilized enzymes could be recycled for four cycles leading each time to a similar amount of vanillin (3.1–3.5 mM).…”

Section: In Vitro Cascades Requiring For Each Step a Biocatalystmentioning

confidence: 99%

Extending Designed Linear Biocatalytic Cascades for Organic Synthesis

2018

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Artificial cascade reactions involving biocatalysts have demonstrated a tremendous potential during the recent years. This review just focuses on selected examples of the last year and putting them into context to a previously published suggestion for classification. Subdividing the cascades according to the number of catalysts in the linear sequence, and classifying whether the steps are performed simultaneous or in a sequential fashion as well as whether the reaction sequence is performed in vitro or in vivo allows to organise the concepts. The last year showed, that combinations of in vivo as well as in vitro are possible. Incompatible reaction steps may be run in a sequential fashion or by compartmentalisation of the incompatible steps either by using special reactors (membrane), polymersomes or flow techniques.

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“…In 2017, Furuya et al . presented a report on immobilizing two Escherichia coli cells expressing oxygenases, Fdc and Cso2, to enable the cascade synthesis of vanillin from ferulic acid via 4‐vinylguaiacol . The lack of studies concerning vanillin synthesis with isolated enzymes may be related to the very limited choice of enzymes with excellent catalytic performance and to their poor commercial availability.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of vanillin and related catalytic mechanism

Liu

Zou

Yao

et al. 2019

Flavour & Fragrance J

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There has been an increasing demand for bio vanillin for a variety of applications. Although vanillin production using biotechnological methods based on microbial fermentation has been extensively explored, the use of isolated enzymes for vanillin synthesis has not yet attracted much attention. Lipoxygenase (LOX) is an iron‐containing dioxygenase well known for catalysing the hydroperoxidation of polyunsaturated fatty acids and esters. Its newly discovered ability to catalyse the oxidative cleavage of isoeugenol to vanillin offers a promising solution for synthesizing bio vanillin. In this study, soybean LOX was used as the catalyst for vanillin synthesis. The reaction was optimised by examining the effects of pH, temperature, substrate concentration, and enzyme dosage. By investigating the impact of various additives, including two denaturants, seven chelators, six surfactants, 10 organic solvents, eight deep eutectic solvents, and 13 natural deep eutectic solvents, it was found that denaturants (urea and guanidine) and some chelators (e.g. ethylenediaminetetraacetic acid, EDTA) are effective in improving synthetic yields, by up to 133 and 406%, respectively, relative to the additive‐free reaction system. Two free‐radical catalytic mechanisms were proposed to explain the new activity of the enzyme for vanillin synthesis.

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Biotechnological production of vanillin using immobilized enzymes

Cited by 81 publications

References 24 publications

Environmental Catalysis: Present and Future

Environmental Catalysis: Present and Future

Extending Designed Linear Biocatalytic Cascades for Organic Synthesis

Enzymatic synthesis of vanillin and related catalytic mechanism

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