Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of
            <i>Cupriavidus basilensis</i>
            HMF14

Koopman, Frank; Wierckx, Nick; Winde, Johannes H. de; Ruijssenaars, Harald J.

doi:10.1073/pnas.0913039107

Cited by 221 publications

(258 citation statements)

References 43 publications

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“…involved in a HMF degradation pathway [32]. More importantly, although the use of AAO for HMF conversion into FDCA is covered by one patent, which also describes use of chloroperoxidase, albeit with very modest FDCA yields in all cases [27], this is the first time that full enzymatic conversion of HMF into FDCA has been reported using a reaction cascade in which the H 2 O 2 generated by AAO during oxidative transformation of HMF into FFCA is used by a peroxygenase to catalyze conversion of the latter compound into FDCA.…”

Section: Discussionmentioning

confidence: 99%

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

Ferreira²,

et al. 2015

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Oxidative conversion of 5-hydroxymethylfurfural (HMF) is of biotechnological interest for the production of renewable (lignocellulose-based) platform chemicals, such as 2,5-furandicarboxylic acid (FDCA). To the best of our knowledge, the ability of fungal aryl-alcohol oxidase (AAO) to oxidize HMF is reported here for the first time, resulting in almost complete conversion into 2,5-formylfurancarboxylic acid (FFCA) in a few hours. The reaction starts with alcohol oxidation, yielding 2,5-diformylfuran (DFF), which is rapidly converted into FFCA by carbonyl oxidation, most probably without leaving the enzyme active site. This agrees with the similar catalytic efficiencies of the enzyme with respect to oxidization of HMF and DFF, and its very low activity on 2,5-hydroxymethylfurancarboxylic acid (which was not detected by GC-MS). However, AAO was found to be unable to directly oxidize the carbonyl group in FFCA, and only modest amounts of FDCA are formed from HMF (most probably by chemical oxidation of FFCA by the H 2 O 2 previously generated by AAO). As aldehyde oxidation by AAO proceeds via the corresponding geminal diols (aldehyde hydrates), the various carbonyl oxidation rates may be related to the low degree of hydration of FFCA compared with DFF. The conversion of HMF was completed by introducing a fungal unspecific heme peroxygenase that uses the H 2 O 2 generated by AAO to transform FFCA into FDCA, albeit more slowly than the previous AAO reactions. By adding this peroxygenase when FFCA production by AAO has been completed, transformation of HMF into FDCA may be achieved in a reaction cascade in which O 2 is the only co-substrate required, and water is the only byproduct formed.

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Section: Discussionmentioning

confidence: 99%

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

Ferreira²,

et al. 2015

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“…An HMF/furfural oxidoreductase from a Cupriavidus basilensis strain has been introduced into Pseudomonas putida S12. 326 The resulting whole-cell biocatalyst produced 30 g/L of 2,5-furandicarboxylic acid from HMF with a yield of 0.97 mol/mol and a productivity of 0.21 g/(L h) under aerobic fed-batch conditions. 327 No residual furan derivatives were found, which is highly beneficial for subsequent purification and polymerization.…”

Section: 5-furandicarboxylic Acidmentioning

confidence: 99%

Transformation of Biomass into Commodity Chemicals Using Enzymes or Cells

2013

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“…Unfortunately, the modes of toxicity of many of these toxins are poorly described, and genes conferring tolerance to many of these compounds have not been identified (18,19). An expanded catalog of tolerance-conferring genotypes may shed light on mechanisms of toxicity and enable synthetic biology approaches for the design of diverse production hosts with broadspectrum tolerance.Soil microorganisms, including white-rot fungi (20) and many bacteria (21), are likely a valuable reservoir of genetic elements that confer tolerance to lignocellulosic inhibitors and next-generation biofuels (22)(23)(24)(25). Indeed, our previous work using largeinsert (40-to 50-kb) functional metagenomic libraries identified three such genes conferring improved tolerance to two biomass inhibitors (19).…”

mentioning

confidence: 99%

“…Soil microorganisms, including white-rot fungi (20) and many bacteria (21), are likely a valuable reservoir of genetic elements that confer tolerance to lignocellulosic inhibitors and next-generation biofuels (22)(23)(24)(25). Indeed, our previous work using largeinsert (40-to 50-kb) functional metagenomic libraries identified three such genes conferring improved tolerance to two biomass inhibitors (19).…”

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confidence: 99%

Identification of Genes Conferring Tolerance to Lignocellulose-Derived Inhibitors by Functional Selections in Soil Metagenomes

Forsberg

Patel

Witt

et al. 2016

Appl Environ Microbiol

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The production of fuels or chemicals from lignocellulose currently requires thermochemical pretreatment to release fermentable sugars. These harsh conditions also generate numerous small-molecule inhibitors of microbial growth and fermentation, limiting production. We applied small-insert functional metagenomic selections to discover genes that confer microbial tolerance to these inhibitors, identifying both individual genes and general biological processes associated with tolerance to multiple inhibitory compounds. Having screened over 248 Gb of DNA cloned from 16 diverse soil metagenomes, we describe gain-of-function tolerance against acid, alcohol, and aldehyde inhibitors derived from hemicellulose and lignin, demonstrating that uncultured soil microbial communities hold tremendous genetic potential to address the toxicity of pretreated lignocellulose. We recovered genes previously known to confer tolerance to lignocellulosic inhibitors as well as novel genes that confer tolerance via unknown functions. For instance, we implicated galactose metabolism in overcoming the toxicity of lignin monomers and identified a decarboxylase that confers tolerance to ferulic acid; this enzyme has been shown to catalyze the production of 4-vinyl guaiacol, a valuable precursor to vanillin production. These metagenomic tolerance genes can enable the flexible design of hardy microbial catalysts, customized to withstand inhibitors abundant in specific bioprocessing applications. Many lignocellulosic feedstocks (e.g., switchgrass) are preferred to maize, sugarcane, and other traditional food crops for the production of fuels and chemicals because they are able to grow on marginal land, often require little attention or energy input, and do not compete directly with the food supply (1-6). However, lignocellulose requires harsh thermochemical pretreatment methods to liberate fermentable monosaccharides (7-9), producing an additional compendium of compounds inhibitory to microbial growth that ultimately reduce production efficiencies (10-12). These small-molecule inhibitors derived from lignocellulose pretreatment (here called lignocellulosic inhibitors) are typically aldehydes, organic acids, furans, or phenolics and can originate from the cellulosic, hemicellulosic, and lignified fractions of the feedstock (11-15).Engineering hardier microbial production hosts with elevated tolerance to these inhibitors offers potential to ameliorate the toxic effects of these compounds without incurring the high process costs associated with detoxifying the lignocellulosic hydrolysate (16, 17). Unfortunately, the modes of toxicity of many of these toxins are poorly described, and genes conferring tolerance to many of these compounds have not been identified (18,19). An expanded catalog of tolerance-conferring genotypes may shed light on mechanisms of toxicity and enable synthetic biology approaches for the design of diverse production hosts with broadspectrum tolerance.Soil microorganisms, including white-rot fungi (20) and many bacteria (21), ar...

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Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14

Cited by 221 publications

References 43 publications

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

Transformation of Biomass into Commodity Chemicals Using Enzymes or Cells

Identification of Genes Conferring Tolerance to Lignocellulose-Derived Inhibitors by Functional Selections in Soil Metagenomes

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