Efficient whole-cell biotransformation of 5-(hydroxymethyl)furfural into FDCA, 2,5-furandicarboxylic acid

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

doi:10.1016/j.biortech.2010.03.050

Cited by 220 publications

(190 citation statements)

References 23 publications

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“…FDCA's main potential lies in its structural analogy to terephthalic acid, and it has been heralded as a bio-based alternative to this oil-based bulk chemical (de Jong et al 2012;Koopman et al 2010a). It can be used for the production of polyesters such as polyethylene-, polypropylene-, and polybutylene-FDCA, which have similar-or even superior-properties to their terephthalate-based counterparts (de Jong et al 2012;Gandini 2011;Moreau et al 2004).…”

Section: Potential Of Bio-based 25-furandicarboxylic Acidmentioning

confidence: 99%

Whole-Cell Biocatalytic Production of 2,5-Furandicarboxylic Acid

Wierckx

Schuurman²,

Blank

et al. 2014

Microorganisms in Biorefineries

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Section: Potential Of Bio-based 25-furandicarboxylic Acidmentioning

confidence: 99%

Whole-Cell Biocatalytic Production of 2,5-Furandicarboxylic Acid

Wierckx

Schuurman²,

Blank

et al. 2014

Microorganisms in Biorefineries

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“…The Pseudomonas strain itself is able to produce HMF acid but not FDCA from HMF. Only when HmfH is expressed in Pseudomonas is FDCA formed (9). On the basis of these findings, it has been suggested that HmfH can perform both alcohol and aldehyde oxidations and therefore may be able to form FDCA from HMF.…”

mentioning

confidence: 99%

Discovery and Characterization of a 5-Hydroxymethylfurfural Oxidase from Methylovorus sp. Strain MP688

Dijkman

Fraaije

2014

Appl Environ Microbiol

125

200

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In the search for useful and renewable chemical building blocks, 5-hydroxymethylfurfural (HMF) has emerged as a very promising candidate, as it can be prepared from sugars. HMF can be oxidized to 2,5-furandicarboxylic acid (FDCA), which is used as a substitute for petroleum-based terephthalate in polymer production. On the basis of a recently identified bacterial degradation pathway for HMF, candidate genes responsible for selective HMF oxidation have been identified. Heterologous expression of a protein from Methylovorus sp. strain MP688 in Escherichia coli and subsequent enzyme characterization showed that the respective gene indeed encodes an efficient HMF oxidase (HMFO). HMFO is a flavin adenine dinucleotide-containing oxidase and belongs to the glucose-methanol-choline-type flavoprotein oxidase family. Intriguingly, the activity of HMFO is not restricted to HMF, as it is active with a wide range of aromatic primary alcohols and aldehydes. The enzyme was shown to be relatively thermostable and active over a broad pH range. This makes HMFO a promising oxidative biocatalyst that can be used for the production of FDCA from HMF, a reaction involving both alcohol and aldehyde oxidations.

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“…[8][9][10] The production of 1 is usually based on processes including the conversion of hexoses under acidic conditions at higher temperatures 10,11 and various oxidation reactions of 2,5-disubstituted furans, mainly 5-(hydroxymethyl)furfural. 10,12,13 published, but these are amongst the less convenient procedures. …”

Section: Introductionmentioning

confidence: 99%

Direct synthesis of furan-2,5-dicarboxylic acid monoamides

Fischer¹,

Fišerová²

2015

Arkivoc

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A regioselective monoamidation of furan-2,5-dicarboxylic acid using O- (benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate is presented. The excellent regioselectivity in favour of activated monobenzotriazoyl ester as a intermediate is achieved by gradual addition of a coupling reagent into a dilute solution of furan-2,5-dicarboxylic acid and N,Ndiisopropylethylamine in dimethylformamide. Divided crude reaction mixture is used directly in the subsequent coupling reactions with benzylamine, diethylamine, piperidine and aniline, respectively. Four representative monoamides are prepared and isolated in very good yields 73-82%. Traces of symmetric diamides were also detected, however never in isolable amounts.

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Efficient whole-cell biotransformation of 5-(hydroxymethyl)furfural into FDCA, 2,5-furandicarboxylic acid

Cited by 220 publications

References 23 publications

Whole-Cell Biocatalytic Production of 2,5-Furandicarboxylic Acid

Whole-Cell Biocatalytic Production of 2,5-Furandicarboxylic Acid

Discovery and Characterization of a 5-Hydroxymethylfurfural Oxidase from Methylovorus sp. Strain MP688

Direct synthesis of furan-2,5-dicarboxylic acid monoamides

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