Whole-cell biocatalytic selective oxidation of 5-hydroxymethylfurfural to 5-hydroxymethyl-2-furancarboxylic acid

Zhang, Xueying; Zong, Min‐Hua; Li, Ning

doi:10.1039/c7gc01751k

Cited by 82 publications

(104 citation statements)

References 49 publications

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“…[106] In line with the current interest in furan dicarboxylic acid (FDCA) as as ubstitute for non-renewable polymer building blocks such as phthalates,arange of biocatalytic transformations of glucose-derived hydroxymethyl furfural (HMF) into FDCA have been developed (Scheme 33). Aside from wholecell approaches, [116] oxidases [117] and combinations of oxidases/ peroxygenases [118] have been employed.…”

Section: Oxidation Of Primary Alcohols To Acidsmentioning

confidence: 99%

Biocatalytic Oxidation Reactions: A Chemist's Perspective

et al. 2018

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Oxidation chemistry using enzymes is approaching maturity and practical applicability in organic synthesis. Oxidoreductases (enzymes catalysing redox reactions) enable chemists to perform highly selective and efficient transformations ranging from simple alcohol oxidations to stereoselective halogenations of non‐activated C−H bonds. For many of these reactions, no “classical” chemical counterpart is known. Hence oxidoreductases open up shorter synthesis routes based on a more direct access to the target products. The generally very mild reaction conditions may also reduce the environmental impact of biocatalytic reactions compared to classical counterparts. In this Review, we critically summarise the most important recent developments in the field of biocatalytic oxidation chemistry and identify the most pressing bottlenecks as well as promising solutions.

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Section: Oxidation Of Primary Alcohols To Acidsmentioning

confidence: 99%

Biocatalytic Oxidation Reactions: A Chemist's Perspective

et al. 2018

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“…In the work of Zhang et al . () the addition of LB broth was beneficial to the improvement in the oxidative capability of HMF by C. testosterone SC1588 (Zhang et al . ).…”

Section: Resultsmentioning

confidence: 99%

“…() the addition of LB broth was beneficial to the improvement in the oxidative capability of HMF by C. testosterone SC1588 (Zhang et al . ). However, our works is not in accordance with their work, which showed a stronger oxidative ability in the presence of LB broth.…”

Section: Resultsmentioning

confidence: 99%

“…Unfortunately, there was no continual improvement in the product ee value and a prolonged reaction time emerged. In the work of Zhang et al (2017) the addition of LB broth was beneficial to the improvement in the oxidative capability of HMF by C. testosterone SC1588 . However, our works is not in accordance with their work, which showed a stronger oxidative ability in the presence of LB broth.…”

Section: Effect Of Co-substrate For the Asymmetric Oxidation Of Racemmentioning

confidence: 99%

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Highly selective resolution of racemic 1‐phenyl‐1,2‐ethanediol by a novel strain Kurthia gibsonii SC 0312

Peng

Zhao

et al. 2019

Lett Appl Microbiol

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Chiral 1‐phenyl‐1,2‐ethanediol (PED) performs vital effect for the preparation of pharmaceuticals, agrochemicals and cosmetics. In the study, a newly isolated strain Kurthia gibsoniiSC0312 with the ability to selectively oxidize racemic PED to achieve (S)‐PED was evaluated in the aqueous reaction system. The strain showed excellent catalytic performances within the range of pH 5·5–8·5, temperature 25–45°C and the amount of cell 15 mg ml−1 to 30 mg ml−1. Besides, 2‐hydroxyacetophenone (HAP) as the oxidation product displayed a stronger inhibition to the catalytic activity of cell, only remaining <63% of catalytic activity after incubation at 40 mmol l−1 HAP for 6 h. For various metal ions, Cu2+ can obviously improve 1·7 times of the catalytic activity of cell at the concentration of 0·2 mmol l−1. Acetone can stimulate the catalytic capacity of cell to improve the optical purity of (S)‐PED at the PED concentration of 80 mmol l−1, up to appropriately 94% from 85·4%; compared to the resting cell, growing cell exerted no positive effect in the yield and optical purity. Finally, a highly effective kinetic resolution system of racemic PED by the new strain was obtained, with the (S)‐PED yield of 41% and optical purity of 94%. Significance and Impact of the Study Biocatalyst is a vital component in the process of biotransformation. There are a growing number of studies of biocatalyst reporting the preparation of enantiomer of 1‐phenyl‐1,2‐ethanediol. And the performance of this preparation reaction is also gradually improving. This study is the first to demonstrate that Kurthia gibsonii can efficiently and selectively oxidize racemic 1‐phenyl‐1,2‐ethanediol, and we assess the effect of various factors on the catalytic performance of the strain. The work adds to a growing body of evidence for using biocatalytic method in the synthesis of chiral 1‐phenyl‐1,2‐ethanediol and provides a probable approach to mine excellent properties of enzymes.

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“…However, in many cases, a close interplay with chemo‐catalysis is essential either to provide certain substrates for further bio‐catalytic transformation or to conduct a chemo‐catalytic upgrading of bio‐catalytically derived compounds. Examples for a chemo‐bio‐catalysis sequence cover the chemo‐catalytic formation of 5‐hydroxymethylfurfural followed by selective bio‐catalytic oxidation to 2,5‐furandicarboxylic acid , , or the chemo‐ or mechano‐catalytic depolymerization of cellulose to celloligomers followed by enzymatic hydrolysis of these celloligomers to glucose . For the former case, bio‐catalysis provides a highly pure monomer for further polymerization but also requires a rather high purity of the feed stream compared to chemo‐catalytic oxidation.…”

Section: Biomass As Renewable Resourcementioning

confidence: 99%

Sustainable Carbon Sources and Renewable Energy: Challenges and Opportunities at the Interface of Catalysis and Reaction Engineering

Palkovits

2018

Chemie Ingenieur Technik

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Limited fossil resources and the need to reduce greenhouse gas emissions require the development of environmentally benign production processes. Economic, energy and carbon‐efficient value chains based on lignocellulosic biomass are essential for a sustainable and potentially CO2‐neutral chemical industry. Biomass presents a concentrated renewable carbon source for base and fine chemicals, polymers and liquid fuels of high energy density. Research studies have highlighted the need for novel process concepts to account for the high degree of functionality of lignocellulosic biomass. Major challenges include selective deoxygenation of the highly functionalized starting materials, energy‐intensive separation and processes bridging chemo‐catalysis, biotechnology and electro‐catalysis. In the following, these challenges are exemplarily discussed. The showcases are selected to illustrate concepts and not meant to provide a comprehensive overview of the field.

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Whole-cell biocatalytic selective oxidation of 5-hydroxymethylfurfural to 5-hydroxymethyl-2-furancarboxylic acid

Abstract: HMF has been efficiently upgraded into HMFCA with a good yield by using a highly HMF-tolerant strain Comamonas testosteroni SC1588.

Cited by 82 publications

References 49 publications

Biocatalytic Oxidation Reactions: A Chemist's Perspective

Biocatalytic Oxidation Reactions: A Chemist's Perspective

Highly selective resolution of racemic 1‐phenyl‐1,2‐ethanediol by a novel strain Kurthia gibsonii SC 0312

Sustainable Carbon Sources and Renewable Energy: Challenges and Opportunities at the Interface of Catalysis and Reaction Engineering

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