Abstract
2,5-Furandicarboxylic acid (FDCA) is attracting increasing attention because of its potential applications as a sustainable substitute to petroleum-derived terephthalic acid for the production of bio-based polymers, such as poly(ethylene 2,5-furandicarboxylate) (PEF). Many catalytic methods have been developed for the synthesis of FDCA, including chemocatalysis, biocatalysis, photocatalysis, and electrocatalysis. Biocatalysis is a promising approach with advantages that include mild reaction condition, lower cost, higher selectivity, and environment amity. However, the biocatalytic production of FDCA has hardly been reviewed. To fully understand the current research developments, this review comprehensively considers the research progress on toxic effects and biodegradation of furan aldehydes, and then summarizes the latest achievements concerning the synthesis of FDCA from 5-hydroxymethylfurfural and other chemicals, such as 2-furoic acid and 5-methoxymethylfurfural. Our primary focus is on biocatalytic methods, including enzymatic catalysis (in vitro) and whole-cell catalysis (in vivo). Furthermore, future research directions and general developmental trends for more efficient biocatalytic production of FDCA are also proposed.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00253-019-10272-9/MediaObjects/253_2019_10272_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00253-019-10272-9/MediaObjects/253_2019_10272_Fig2_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00253-019-10272-9/MediaObjects/253_2019_10272_Fig3_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00253-019-10272-9/MediaObjects/253_2019_10272_Fig4_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00253-019-10272-9/MediaObjects/253_2019_10272_Fig5_HTML.png)
Similar content being viewed by others
References
Ahmad FB, Zhang Z, Doherty WOS, O'Hara IM (2019) The outlook of the production of advanced fuels and chemicals from integrated oil palm biomass biorefinery. Renew Sust Energ Rev 109:386–411. https://doi.org/10.1016/j.rser.2019.04.009
Ait Rass H, Essayem N, Besson M (2015) Selective aerobic oxidation of 5-HMF into 2,5-furandicarboxylic acid with Pt catalysts supported on TiO2- and ZrO2-based supports. ChemSusChem 8(7):1206–1217. https://doi.org/10.1002/cssc.201403390
Allen SA, Clark W, McCaffery JM, Cai Z, Lanctot A, Slininger PJ, Liu ZL, Gorsich SW (2010) Furfural induces reactive oxygen species accumulation and cellular damage in Saccharomyces cerevisiae. Biotechnol Biofuels 3(1):2. https://doi.org/10.1186/1754-6834-3-2
Almeida JR, Bertilsson M, Gorwa-Grauslund MF, Gorsich S, Lidén G (2009) Metabolic effects of furaldehydes and impacts on biotechnological processes. Appl Microbiol Biotechnol 82(4):625–638. https://doi.org/10.1007/s00253-009-1875-1
Antonyraj CA, Huynh NTT, Park S-K, Shin S, Kim YJ, Kim S, Lee K-Y, Cho JK (2017) Basic anion-exchange resin (AER)-supported Au-Pd alloy nanoparticles for the oxidation of 5-hydroxymethyl-2-furfural (HMF) into 2,5-furan dicarboxylic acid (FDCA). Appl Catal A Gen 547:230–236. https://doi.org/10.1016/j.apcata.2017.09.012
Ball GL, McLellan CJ, Bhat VS (2012) Toxicological review and oral risk assessment of terephthalic acid (TPA) and its esters: a category approach. Crit Rev Toxicol 42(1):28–67. https://doi.org/10.3109/10408444.2011.623149
Banerjee A, Dick GR, Yoshino T, Kanan MW (2016) Carbon dioxide utilization via carbonate-promoted C–H carboxylation. Nature 531:215–219. https://doi.org/10.1038/nature17185
Barwe S, Weidner J, Cychy S, Morales DM, Dieckhofer S, Hiltrop D, Masa J, Muhler M, Schuhmann W (2018) Electrocatalytic oxidation of 5-(hydroxymethyl)furfural using high-surface-area nickel boride. Angew Chem Int Ed 57(35):11460–11464. https://doi.org/10.1002/anie.201806298
Boopathy R, Daniels L (1991) Isolation and characterization of a furfural degrading sulfate-reducing bacterium from an anaerobic digester. Curr Microbiol 23(6):327–332. https://doi.org/10.1007/bf02104134
Boopathy R, Bokang H, Daniels L (1993) Biotransformation of furfural and 5-hydroxymethyl furfural by enteric bacteria. J Ind Microbiol 11(3):147–150. https://doi.org/10.1007/bf01583715
Brune G, Schoberth SM, Sahm H (1983) Growth of a strictly anaerobic bacterium on furfural (2-furaldehyde). Appl Environ Microbiol 46(5):1187–1192 https://aem.asm.org/content/aem/46/5/1187.full.pdf. Accessed 29 Sept 2019
Caes BR, Teixeira RE, Knapp KG, Raines RT (2015) Biomass to furanics: renewable routes to chemicals and fuels. ACS Sustain Chem Eng 3(11):2591–2605. https://doi.org/10.1021/acssuschemeng.5b00473
Cantarella M, Cantarella L, Gallifuoco A, Spera A, Alfani F (2004) Comparison of different detoxification methods for steam-exploded poplar wood as a substrate for the bioproduction of ethanol in SHF and SSF. Process Biochem 39(11):1533–1542. https://doi.org/10.1016/S0032-9592(03)00285-1
Carro J, Ferreira P, Rodríguez L, Prieto A, Serrano A, Balcells B, Ardá A, Jiménez-Barbero J, Gutiérrez A, Ullrich R, Hofrichter M, Martínez AT (2015) 5-Hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase. FEBS J 282(16):3218–3229. https://doi.org/10.1111/febs.13177
Carro J, Fernández-Fueyo E, Fernández-Alonso C, Cañada J, Ullrich R, Hofrichter M, Alcalde M, Ferreira P, Martínez AT (2018) Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural. Biotechnol Biofuels 11(1):86. https://doi.org/10.1186/s13068-018-1091-2
Casanova O, Iborra S, Corma A (2009) Biomass into chemicals: aerobic oxidation of 5-hydroxymethyl-2-furfural into 2,5-furandicarboxylic acid with gold nanoparticle catalysts. ChemSusChem 2(12):1138–1144. https://doi.org/10.1002/cssc.200900137
Chen PX, Tang Y, Zhang B, Liu R, Marcone MF, Li X, Tsao R (2014) 5-Hydroxymethyl-2-furfural and derivatives formed during acid hydrolysis of conjugated and bound phenolics in plant foods and the effects on phenolic content and antioxidant capacity. J Agric Food Chem 62(20):4754–4761. https://doi.org/10.1021/jf500518r
Chen G, van Straalen NM, Roelofs D (2016) The ecotoxicogenomic assessment of soil toxicity associated with the production chain of 2,5-furandicarboxylic acid (FDCA), a candidate bio-based green chemical building block. Green Chem 18(16):4420–4431. https://doi.org/10.1039/C6GC00430J
Chen G, Wu L, Fan H, B-g L (2018) Highly efficient two-step synthesis of 2,5-furandicarboxylic acid from fructose without 5-hydroxymethylfurfural (HMF) separation: in situ oxidation of HMF in alkaline aqueous H2O/DMSO mixed solvent under mild conditions. Ind Eng Chem Res 57(48):16172–16181. https://doi.org/10.1021/acs.iecr.8b03589
Choi S, Song CW, Shin JH, Lee SY (2015) Biorefineries for the production of top building block chemicals and their derivatives. Metab Eng 28:223–239. https://doi.org/10.1016/j.ymben.2014.12.007
Dick GR, Frankhouser AD, Banerjee A, Kanan MW (2017) A scalable carboxylation route to furan-2,5-dicarboxylic acid. Green Chem 19(13):2966–2972. https://doi.org/10.1039/C7GC01059A
Dijkman WP, Fraaije MW (2014) Discovery and characterization of a 5-hydroxymethylfurfural oxidase from Methylovorus sp. strain MP688. Appl Environ Microbiol 80(3):1082–1090. https://doi.org/10.1128/AEM.03740-13
Dijkman WP, de Gonzalo G, Mattevi A, Fraaije MW (2013) Flavoprotein oxidases: classification and applications. Appl Microbiol Biotechnol 97(12):5177–5188. https://doi.org/10.1007/s00253-013-4925-7
Dijkman WP, Groothuis DE, Fraaije MW (2014) Enzyme-catalyzed oxidation of 5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid. Angew Chem Int Ed 53(25):6515–6518. https://doi.org/10.1002/anie.201402904
Dijkman WP, Binda C, Fraaije MW, Mattevi A (2015) Structure-based enzyme tailoring of 5-hydroxymethylfurfural oxidase. ACS Catal 5(3):1833–1839. https://doi.org/10.1021/acscatal.5b00031
Ding X, Wang MY, Yao YX, Li GY, Cai BC (2010) Protective effect of 5-hydroxymethylfurfural derived from processed Fructus Corni on human hepatocyte LO2 injured by hydrogen peroxide and its mechanism. J Ethnopharmacol 128(2):373–376. https://doi.org/10.1016/j.jep.2010.01.043
Domínguez de María P, Guajardo N (2017) Biocatalytic valorization of furans: opportunities for inherently unstable substrates. ChemSusChem 10(21):4123–4134. https://doi.org/10.1002/cssc.201701583
Douša M, Gibala P, Břicháč J, Havlíček J (2012) The formation of furfural compounds in selected saccharide- and polysaccharide-based pharmaceutical excipients. J Pharm Sci 101(5):1811–1820. https://doi.org/10.1002/jps.23072
Feldman D, Kowbel DJ, Glass NL, Yarden O, Hadar Y (2015) Detoxification of 5-hydroxymethylfurfural by the Pleurotus ostreatus lignolytic enzymes aryl alcohol oxidase and dehydrogenase. Biotechnol Biofuels 8(1):63. https://doi.org/10.1186/s13068-015-0244-9
Flaschenträger B, Wahhab SMA (1960) An improved method for the isolation and estimation of furan-2, 5-dicarboxylic acid in human urine. Microchim Acta 48(2):275–281. https://doi.org/10.1007/BF01215794
Folkerts M, Ney U, Kneifel H, Stackebrandt E, Witte EG, Förstel H, Schoberth SM, Sahm H (1989) Desulfovibrio furfuralis sp. nov., a furfural degrading strictly anaerobic bacterium. Syst Appl Microbiol 11(2):161–169. https://doi.org/10.1016/S0723-2020(89)80056-6
Fonseca BG, de Oliveira MR, de Oliveira FF, Vieira ER, Nogueira AS, Baratella BF, Rodrigues LC, Hou-Rui Z, Da Silva SS (2011) Biological detoxification of different hemicellulosic hydrolysates using Issatchenkia occidentalis CCTCC M 206097 yeast. J Ind Microbiol Biotechnol 38(1):199–207. https://doi.org/10.1007/s10295-010-0845-z
Galkin KI, Krivodaeva EA, Romashov LV, Zalesskiy SS, Kachala VV, Burykina JV, Ananikov VP (2016) Critical influence of 5-hydroxymethylfurfural aging and decomposition on the utility of biomass conversion in organic synthesis. Angew Chem Int Ed 55(29):8338–8342. https://doi.org/10.1002/anie.201602883
Godan TK, Rajesh RO, Loreni PC, Kumar Rai A, Sahoo D, Pandey A, Binod P (2019) Biotransformation of 5-hydroxymethylfurfural by Acinetobacter oleivorans S27 for the synthesis of furan derivatives. Bioresour Technol 282:88–93. https://doi.org/10.1016/j.biortech.2019.02.125
Gorbanev YY, Kegnæs S, Riisager A (2011) Selective aerobic oxidation of 5-hydroxymethylfurfural in water over solid ruthenium hydroxide catalysts with magnesium-based supports. Catal Lett 141(12):1752–1760. https://doi.org/10.1007/s10562-011-0707-y
Guarnieri MT, Ann Franden M, Johnson CW, Beckham GT (2017) Conversion and assimilation of furfural and 5-(hydroxymethyl)furfural by Pseudomonas putida KT2440. Metab Eng Commun 4:22–28. https://doi.org/10.1016/j.meteno.2017.02.001
Gutiérrez T, Buszko ML, Ingram LO, Preston JF (2002) Reduction of furfural to furfuryl alcohol by ethanologenic strains of bacteria and its effect on ethanol production from xylose. In: Biotechnology for fuels and chemicals: the twenty–third symposium. Humana, Totowa, NJ, pp 327–340. https://doi.org/10.1007/978-1-4612-0119-9_27
Gutiérrez T, Ingram LO, Preston JF (2006) Purification and characterization of a furfural reductase (FFR) from Escherichia coli strain LYO1—an enzyme important in the detoxification of furfural during ethanol production. J Biotechnol 121(2):154–164. https://doi.org/10.1016/j.jbiotec.2005.07.003
Hadi S, Rehman A (1989) Specificity of the interaction of furfural with DNA. Mutat Res Lett 225(3):101–106. https://doi.org/10.1016/0165-7992(89)90125-5
Han X, Li C, Liu X, **a Q, Wang Y (2017) Selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over MnOx–CeO2 composite catalysts. Green Chem 19(4):996–1004. https://doi.org/10.1039/c6gc03304k
Hayashi E, Komanoya T, Kamata K, Hara M (2017) Heterogeneously-catalyzed aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid with MnO2. ChemSusChem 10(4):654–658. https://doi.org/10.1002/cssc.201601443
He Y-C, Jiang C-X, Chong G-G, Di J-H, Ma C-L (2018) Biological synthesis of 2,5-bis (hydroxymethyl) furan from biomass-derived 5-hydroxymethylfurfural by E. coli CCZU-K14 whole cells. Bioresour Technol 247:1215–1220. https://doi.org/10.1016/j.biortech.2017.09.071
Heer D, Sauer U (2008) Identification of furfural as a key toxin in lignocellulosic hydrolysates and evolution of a tolerant yeast strain. Microb Biotechnol 1(6):497–506. https://doi.org/10.1111/j.1751-7915.2008.00050.x
Hossain GS, Yuan H, Li J, H-d S, Wang M, Du G, Chen J, Liu L (2017) Metabolic engineering of Raoultella ornithinolytica BF60 for the production of 2, 5-furandicarboxylic acid from 5-hydroxymethylfurfural. Appl Environ Microbiol 83(1):e02312–e02316. https://doi.org/10.1128/AEM.02312-16
Hu L, Zhao G, Hao W, Tang X, Sun Y, Lin L, Liu S (2012) Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes. RSC Adv 2(30):11184–11206. https://doi.org/10.1039/C2RA21811A
Hu L, He A, Liu X, **a J, Xu J, Zhou S, Xu J (2018) Biocatalytic transformation of 5-hydroxymethylfurfural into high-value derivatives: recent advances and future aspects. ACS Sustain Chem Eng 6(12):15915–15935. https://doi.org/10.1021/acssuschemeng.8b04356
Husøy T, Haugen M, Murkovic M, Jöbstl D, Stølen LH, Bjellaas T, Rønningborg C, Glatt H, Alexander J (2008) Dietary exposure to 5-hydroxymethylfurfural from Norwegian food and correlations with urine metabolites of short-term exposure. Food Chem Toxicol 46(12):3697–3702. https://doi.org/10.1016/j.fct.2008.09.048
Iwaki A, Kawai T, Yamamoto Y, Izawa S (2013) Biomass conversion inhibitors furfural and 5-hydroxymethylfurfural induce formation of messenger RNP granules and attenuate translation activity in Saccharomyces cerevisiae. Appl Environ Microbiol 79(5):1661–1667. https://doi.org/10.1128/aem.02797-12
Jönsson LJ, Alriksson B, Nilvebrant N-O (2013) Bioconversion of lignocellulose: inhibitors and detoxification. Biotechnol Biofuels 6(1):16. https://doi.org/10.1186/1754-6834-6-16
Kamani MH, Eş I, Lorenzo JM, Remize F, Roselló-Soto E, Barba FJ, Clark J, Mousavi Khaneghah A (2019) Advances in plant materials, food by-products, and algae conversion into biofuels: use of environmentally friendly technologies. Green Chem 21(12):3213–3231. https://doi.org/10.1039/C8GC03860K
Kanner J, Harel S, Fishbein Y, Shalom P (1981) Furfural accumulation in stored orange juice concentrates. J Agric Food Chem 29(5):948–949. https://doi.org/10.1021/jf00107a015
Karich A, Kleeberg S, Ullrich R, Hofrichter M (2018) Enzymatic preparation of 2,5-furandicarboxylic acid (FDCA)-a substitute of terephthalic acid-by the joined action of three fungal enzymes. Microorganisms 6(1):5. https://doi.org/10.3390/microorganisms6010005
Kawarada A, Takahashi N, Kitamura H, Seta Y, Takai M, Tamura S (1955) Biochemical studies on “bakanae” fungus. Part 33. Bull Agric Chem Soc Jpn 19(1):84–86. https://doi.org/10.1080/03758397.1955.10857268
Khan Q, Hadi S (1993) Effect of furfural on plasmid DNA. Biochem Mol Biol Int 29(6):1153–1160 https://europepmc.org/abstract/med/8330021. Accessed 29 Sept 2019
Kieslich K (1976) Microbial transformations of non-steroid cycle compounds. Wiley. https://doi.org/10.1016/0968-0004(77)90053-6
Koenig K, Andreesen JR (1990) Xanthine dehydrogenase and 2-furoyl-coenzyme A dehydrogenase from Pseudomonas putida Fu1: two molybdenum-containing dehydrogenases of novel structural composition. J Bacteriol 172(10):5999–6009. https://doi.org/10.1128/jb.172.10.5999-6009.1990
Koopman F, Wierckx N, de Winde JH, Ruijssenaars HJ (2010a) Efficient whole-cell biotransformation of 5-(hydroxymethyl)furfural into FDCA, 2,5-furandicarboxylic acid. Bioresour Technol 101(16):6291–6296. https://doi.org/10.1016/j.biortech.2010.03.050
Koopman F, Wierckx N, de Winde JH, Ruijssenaars HJ (2010b) Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14. Proc Natl Acad Sci U S A 107(11):4919–4924. https://doi.org/10.1073/pnas.0913039107
Krystof M, Pérez-Sánchez M, Domínguez de María P (2013) Lipase-mediated selective oxidation of furfural and 5-hydroxymethylfurfural. ChemSusChem 6(5):826–830. https://doi.org/10.1002/cssc.201200954
Kumar V, Ashok S, Park S (2013) Recent advances in biological production of 3-hydroxypropionic acid. Biotechnol Adv 31(6):945–961. https://doi.org/10.1016/j.biotechadv.2013.02.008
Laadan B, Almeida JRM, Rådström P, Hahn-Hägerdal B, Gorwa-Grauslund M (2008) Identification of an NADH-dependent 5-hydroxymethylfurfural-reducing alcohol dehydrogenase in Saccharomyces cerevisiae. Yeast 25(3):191–198. https://doi.org/10.1002/yea.1578
Ladkau N, Schmid A, Bühler B (2014) The microbial cell-functional unit for energy dependent multistep biocatalysis. Curr Opin Biotechnol 30:178–189. https://doi.org/10.1016/j.copbio.2014.06.003
Lange J-P, van der Heide E, van Buijtenen J, Price R (2012) Furfural—a promising platform for lignocellulosic biofuels. ChemSusChem 5(1):150–166. https://doi.org/10.1002/cssc.201100648
Lee SA, Wrona LJ, Cahoon AB, Crigler J, Eiteman MA, Altman E (2016) Isolation and characterization of bacteria that use furans as the sole carbon source. Appl Biochem Biotechnol 178(1):76–90. https://doi.org/10.1007/s12010-015-1859-9
Lewis Liu Z, Moon J, Andersh BJ, Slininger PJ, Weber S (2008) Multiple gene-mediated NAD(P)H-dependent aldehyde reduction is a mechanism of in situ detoxification of furfural and 5-hydroxymethylfurfural by Saccharomyces cerevisiae. Appl Microbiol Biotechnol 81(4):743–753. https://doi.org/10.1007/s00253-008-1702-0
Leys D (2018) Flavin metamorphosis: cofactor transformation through prenylation. Curr Opin Chem Biol 47:117–125. https://doi.org/10.1016/j.cbpa.2018.09.024
Li X, Yang R, Ma M, Wang X, Tang J, Zhao X, Zhang X (2015) A novel aldehyde reductase encoded by YML131W from Saccharomyces cerevisiae confers tolerance to furfural derived from lignocellulosic biomass conversion. BioEnergy Res 8(1):119–129. https://doi.org/10.1007/s12155-014-9506-9
Li Y-M, Zhang X-Y, Li N, Xu P, Lou W-Y, Zong M-H (2017) Biocatalytic reduction of HMF to 2,5-bis (hydroxymethyl) furan by HMF-tolerant whole cells. ChemSusChem 10(2):372–378. https://doi.org/10.1002/cssc.201601426
Lin B, Tao Y (2017) Whole-cell biocatalysts by design. Microb Cell Factories 16(1):106. https://doi.org/10.1186/s12934-017-0724-7
Liu ZL, Slininger PJ, Dien BS, Berhow MA, Kurtzman CP, Gorsich SW (2004) Adaptive response of yeasts to furfural and 5-hydroxymethylfurfural and new chemical evidence for HMF conversion to 2,5-bis-hydroxymethylfuran. J Ind Microbiol Biotechnol 31(8):345–352. https://doi.org/10.1007/s10295-004-0148-3
Liu ZL, Slininger PJ, Gorsich SW (2005) Enhanced biotransformation of furfural and hydroxymethylfurfural by newly developed ethanologenic yeast strains. Appl Biochem Biotechnol 121(1):451–460. https://doi.org/10.1385/abab:121:1-3:0451
Liu C, Wu S, Zhang H, **ao R (2019) Catalytic oxidation of lignin to valuable biomass-based platform chemicals: a review. Fuel Process Technol 191:181–201. https://doi.org/10.1016/j.fuproc.2019.04.007
López MJ, Nichols NN, Dien BS, Moreno J, Bothast RJ (2004) Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates. Appl Microbiol Biotechnol 64(1):125–131. https://doi.org/10.1007/s00253-003-1401-9
Marshall SA, Payne KAP, Leys D (2017) The UbiX-UbiD system: the biosynthesis and use of prenylated flavin (prFMN). Arch Biochem Biophys 632:209–221. https://doi.org/10.1016/j.abb.2017.07.014
McKenna SM, Leimkuehler S, Herter S, Turner NJ, Carnell AJ (2015) Enzyme cascade reactions: synthesis of furandicarboxylic acid (FDCA) and carboxylic acids using oxidases in tandem. Green Chem 17(6):3271–3275. https://doi.org/10.1039/c5gc00707k
McKenna SM, Mines P, Law P, Kovacs-Schreiner K, Birmingham WR, Turner NJ, Leimkühler S, Carnell AJ (2017) The continuous oxidation of HMF to FDCA and the immobilisation and stabilisation of periplasmic aldehyde oxidase (PaoABC). Green Chem 19(19):4660–4665. https://doi.org/10.1039/C7GC01696D
Miao Z, Zhang Y, Pan X, Wu T, Zhang B, Li J, Yi T, Zhang Z, Yang X (2015) Superior catalytic performance of Ce1−xBixO2−δ solid solution and Au/Ce1−xBixO2−δ for 5-hydroxymethylfurfural conversion in alkaline aqueous solution. Catal Sci Technol 5(2):1314–1322. https://doi.org/10.1039/C4CY01060D
Michail K, Matzi V, Maier A, Herwig R, Greilberger J, Juan H, Kunert O, Wintersteiger R (2007) Hydroxymethylfurfural: an enemy or a friendly xenobiotic? A bioanalytical approach. Anal Bioanal Chem 387(8):2801–2814. https://doi.org/10.1007/s00216-007-1121-6
Mika LT, Cséfalvay E, Németh Á (2018) Catalytic conversion of carbohydrates to initial platform chemicals: chemistry and sustainability. Chem Rev 118(2):505–613. https://doi.org/10.1021/acs.chemrev.7b00395
Miller EN, Jarboe LR, Turner PC, Pharkya P, Yomano LP, York SW, Nunn D, Shanmugam KT, Ingram LO (2009) Furfural inhibits growth by limiting sulfur assimilation in ethanologenic Escherichia coli strain LY180. Appl Environ Microbiol 75(19):6132–6141. https://doi.org/10.1128/aem.01187-09
Mitsukura K, Sato Y, Yoshida T, Nagasawa T (2004) Oxidation of heterocyclic and aromatic aldehydes to the corresponding carboxylic acids by Acetobacter and Serratia strains. Biotechnol Lett 26(21):1643–1648. https://doi.org/10.1007/s10529-004-3513-4
Modig T, Liden G, Taherzadeh MJ (2002) Inhibition effects of furfural on alcohol dehydrogenase, aldehyde dehydrogenase and pyruvate dehydrogenase. Biochem J 363(3):769–776. https://doi.org/10.1042/0264-6021:3630769
Moreau C, Belgacem MN, Gandini A (2004) Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers. Top Catal 27(1):11–30. https://doi.org/10.1023/B:TOCA.0000013537.13540.0e
Motagamwala AH, Won W, Sener C, Alonso DM, Maravelias CT, Dumesic JA (2018) Toward biomass-derived renewable plastics: production of 2,5-furandicarboxylic acid from fructose. Sci Adv 4(1):eaap9722. https://doi.org/10.1126/sciadv.aap9722
Muñoz De Diego C, Dam MA, Gruter GJM (2013) Method for the preparation of 2,5-furandicarboxylic acid and esters thereof. United States Patent, 8519167B2
Murkovic M, Pichler N (2006) Analysis of 5-hydroxymethylfurfual in coffee, dried fruits and urine. Mol Nutr Food Res 50(9):842–846. https://doi.org/10.1002/mnfr.200500262
Mussatto SI, Roberto IC (2004) Alternatives for detoxification of diluted-acid lignocellulosic hydrolyzates for use in fermentative processes: a review. Bioresour Technol 93(1):1–10. https://doi.org/10.1016/j.biortech.2003.10.005
Nduko JM, Suzuki W, Ki M, Kobayashi H, Ooi T, Fukuoka A, Taguchi S (2012) Polyhydroxyalkanoates production from cellulose hydrolysate in Escherichia coli LS5218 with superior resistance to 5-hydroxymethylfurfural. J Biosci Bioeng 113(1):70–72. https://doi.org/10.1016/j.jbiosc.2011.08.021
Nichols NN, Sharma LN, Mowery RA, Chambliss CK, van Walsum GP, Dien BS, Iten LB (2008) Fungal metabolism of fermentation inhibitors present in corn stover dilute acid hydrolysate. Enzym Microb Technol 42(7):624–630. https://doi.org/10.1016/j.enzmictec.2008.02.008
Okuda N, Soneura M, Ninomiya K, Katakura Y, Shioya S (2008) Biological detoxification of waste house wood hydrolysate using Ureibacillus thermosphaericus for bioethanol production. J Biosci Bioeng 106(2):128–133. https://doi.org/10.1263/jbb.106.128
Parawira W, Tekere M (2011) Biotechnological strategies to overcome inhibitors in lignocellulose hydrolysates for ethanol production: review. Crit Rev Biotechnol 31(1):20–31. https://doi.org/10.3109/07388551003757816
Payne KAP, Marshall SA, Fisher K, Cliff MJ, Cannas DM, Yan C, Heyes DJ, Parker DA, Larrosa I, Leys D (2019) Enzymatic carboxylation of 2-furoic acid yields 2,5-furandicarboxylic acid (FDCA). ACS Catal 9(4):2854–2865. https://doi.org/10.1021/acscatal.8b04862
Qin Y-Z, Li Y-M, Zong M-H, Wu H, Li N (2015) Enzyme-catalyzed selective oxidation of 5-hydroxymethylfurfural (HMF) and separation of HMF and 2,5-diformylfuran using deep eutectic solvents. Green Chem 17(7):3718–3722. https://doi.org/10.1039/C5GC00788G
Quesada Granados J, Villalón Mir M, López García-Serrana H, López Martínez MC (1996) Influence of aging factors on the furanic aldehyde contents of matured brandies: aging markers. J Agric Food Chem 44(6):1378–1381. https://doi.org/10.1021/jf9501103
Ra CH, Jeong G-T, Shin MK, Kim S-K (2013) Biotransformation of 5-hydroxymethylfurfural (HMF) by Scheffersomyces stipitis during ethanol fermentation of hydrolysate of the seaweed Gelidium amansii. Bioresour Technol 140:421–425. https://doi.org/10.1016/j.biortech.2013.04.122
Rajesh RO, Godan TK, Rai AK, Sahoo D, Pandey A, Binod P (2019) Biosynthesis of 2,5-furan dicarboxylic acid by Aspergillus flavus APLS-1: process optimization and intermediate product analysis. Bioresour Technol 284:155–160. https://doi.org/10.1016/j.biortech.2019.03.105
Ramírez-Jiménez A, Guerra-Hernández E, García-Villanova B (2000) Browning indicators in bread. J Agric Food Chem 48(9):4176–4181. https://doi.org/10.1021/jf9907687
Ran H, Zhang J, Gao Q, Lin Z, Bao J (2014) Analysis of biodegradation performance of furfural and 5-hydroxymethylfurfural by Amorphotheca resinae ZN1. Biotechnol Biofuels 7(1):51. https://doi.org/10.1186/1754-6834-7-51
Reynolds S, Stowers S, Patterson R, Maronpot R, Aaronson S, Anderson M (1987) Activated oncogenes in B6C3F1 mouse liver tumors: implications for risk assessment. Science 237(4820):1309–1316. https://doi.org/10.1126/science.3629242
Rodriguez-Arnaiz R, Morales PR, Zimmering S (1992) Evaluation in Drosophila melanogaster of the mutagenic potential of furfural in the mei-9a test for chromosome loss in germ-line cells and the wing spot test for mutational activity in somatic cells. Mutat Res/Genet Toxicol 280(2):75–80. https://doi.org/10.1016/0165-1218(92)90001-G
Rose M, Weber D, Lotsch BV, Kremer RK, Goddard R, Palkovits R (2013) Biogenic metal–organic frameworks: 2,5-furandicarboxylic acid as versatile building block. Microporous Mesoporous Mater 181:217–221. https://doi.org/10.1016/j.micromeso.2013.06.039
Rudroff F, Mihovilovic MD, Gröger H, Snajdrova R, Iding H, Bornscheuer UT (2018) Opportunities and challenges for combining chemo- and biocatalysis. Nat Catal 1(1):12–22. https://doi.org/10.1038/s41929-017-0010-4
Sajid M, Zhao X, Liu D (2018) Production of 2,5-furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF): recent progress focusing on the chemical-catalytic routes. Green Chem 20(24):5427–5453. https://doi.org/10.1039/C8GC02680G
Sárvári Horváth I, Franzén CJ, Taherzadeh MJ, Niklasson C, Lidén G (2003) Effects of furfural on the respiratory metabolism of Saccharomyces cerevisiae in glucose-limited chemostats. Appl Environ Microbiol 69(7):4076–4086. https://doi.org/10.1128/aem.69.7.4076-4086.2003
Sasaki C, Sumimoto K, Asada C, Nakamura Y (2012) Direct hydrolysis of cellulose to glucose using ultra-high temperature and pressure steam explosion. Carbohydr Polym 89(1):298–301. https://doi.org/10.1016/j.carbpol.2012.02.040
Scordia D, Cosentino SL, Jeffries TW (2013) Effectiveness of dilute oxalic acid pretreatment of Miscanthus × giganteus biomass for ethanol production. Biomass Bioenergy 59:540–548. https://doi.org/10.1016/j.biombioe.2013.09.011
Sheldon RA (2014) Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem 16(3):950–963. https://doi.org/10.1039/C3GC41935E
Sheldon RA, Woodley JM (2018) Role of biocatalysis in sustainable chemistry. Chem Rev 118(2):801–838. https://doi.org/10.1021/acs.chemrev.7b00203
Shuai L, Questell-Santiago YM, Luterbacher JS (2016) A mild biomass pretreatment using γ-valerolactone for concentrated sugar production. Green Chem 18(4):937–943. https://doi.org/10.1039/C5GC02489G
Siyo B, Schneider M, Radnik J, Pohl M-M, Langer P, Steinfeldt N (2014) Influence of support on the aerobic oxidation of HMF into FDCA over preformed Pd nanoparticle based materials. Appl Catal A Gen 478:107–116. https://doi.org/10.1016/j.apcata.2014.03.020
Sousa AF, Vilela C, Fonseca AC, Matos M, Freire CSR, Gruter G-JM, Coelho JFJ, Silvestre AJD (2015) Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency. Polym Chem 6(33):5961–5983. https://doi.org/10.1039/C5PY00686D
Sumiki Y (1931) Studies on the fermentation products by mould fungi. Part IX. J Agric Chem Soc Jpn 7(4–8):62–63. https://doi.org/10.1080/03758397.1929.10856900
Tammaro L, Vittoria V, Bugatti V (2014) Dispersion of modified layered double hydroxides in poly (ethylene terephthalate) by high energy ball milling for food packaging applications. Eur Polym J 52:172–180. https://doi.org/10.1016/j.eurpolymj.2014.01.001
Trudgill PW (1969) The metabolism of 2-furoic acid by Pseudomonas F2. Biochem J 113(4):577–587. https://doi.org/10.1042/bj1130577
Tsuge Y, Hori Y, Kudou M, Ishii J, Hasunuma T, Kondo A (2014) Detoxification of furfural in Corynebacterium glutamicum under aerobic and anaerobic conditions. Appl Microbiol Biotechnol 98(20):8675–8683. https://doi.org/10.1007/s00253-014-5924-z
Ullrich R, Nüske J, Scheibner K, Spantzel J, Hofrichter M (2004) Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes. Appl Environ Microbiol 70(8):4575–4581. https://doi.org/10.1128/aem.70.8.4575-4581.2004
van Deurzen MPJ, van Rantwijk F, Sheldon RA (1997) Chloroperoxidase-catalyzed oxidation of 5-hydroxymethylfurfural. J Carbohydr Chem 16(3):299–309. https://doi.org/10.1080/07328309708006531
van Putten R-J, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG (2013) Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem Rev 113(3):1499–1597. https://doi.org/10.1021/cr300182k
Vilela C, Sousa AF, Fonseca AC, Serra AC, Coelho JFJ, Freire CSR, Silvestre AJD (2014) The quest for sustainable polyesters—insights into the future. Polym Chem 5(9):3119. https://doi.org/10.1039/c3py01213a
Wachtmeister J, Rother D (2016) Recent advances in whole cell biocatalysis techniques bridging from investigative to industrial scale. Curr Opin Biotechnol 42:169–177. https://doi.org/10.1016/j.copbio.2016.05.005
Wan X, Zhou C, Chen J, Deng W, Zhang Q, Yang Y, Wang Y (2014) Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au–Pd alloy nanoparticles. ACS Catal 4(7):2175–2185. https://doi.org/10.1021/cs5003096
Wang X, Gao Q, Bao J (2015) Transcriptional analysis of Amorphotheca resinae ZN1 on biological degradation of furfural and 5-hydroxymethylfurfural derived from lignocellulose pretreatment. Biotechnol Biofuels 8(1):136. https://doi.org/10.1186/s13068-015-0323-y
Wang S, Cheng G, Joshua C, He Z, Sun X, Li R, Liu L, Yuan Q (2016) Furfural tolerance and detoxification mechanism in Candida tropicalis. Biotechnol Biofuels 9(1):250. https://doi.org/10.1186/s13068-016-0668-x
Wang K-F, C-l L, K-y S, Guo C, Liu C-Z (2018) Efficient catalytic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid by magnetic laccase catalyst. ChemBioChem 19(7):654–659. https://doi.org/10.1002/cbic.201800008
Wang H, Zhu C, Li D, Liu Q, Tan J, Wang C, Cai C, Ma L (2019) Recent advances in catalytic conversion of biomass to 5-hydroxymethylfurfural and 2, 5-dimethylfuran. Renew Sust Energ Rev 103:227–247. https://doi.org/10.1016/j.rser.2018.12.010
Werpy T, Petersen G (2004) Top value added chemicals from biomass: volume I—results of screening for potential candidates from sugars and synthesis gas. U.S. Department of Energy
Wettstein SG, Alonso DM, Gürbüz EI, Dumesic JA (2012) A roadmap for conversion of lignocellulosic biomass to chemicals and fuels. Curr Opin Chem Eng 1(3):218–224. https://doi.org/10.1016/j.coche.2012.04.002
Wierckx N, Koopman F, Bandounas L, De Winde JH, Ruijssenaars HJ (2010) Isolation and characterization of Cupriavidus basilensis HMF14 for biological removal of inhibitors from lignocellulosic hydrolysate. Microb Biotechnol 3(3):336–343. https://doi.org/10.1111/j.1751-7915.2009.00158.x
Wierckx N, Koopman F, Ruijssenaars HJ, de Winde JH (2011) Microbial degradation of furanic compounds: biochemistry, genetics, and impact. Appl Microbiol Biotechnol 92(6):1095–1105. https://doi.org/10.1007/s00253-011-3632-5
Xu S, Zhou P, Zhang Z, Yang C, Zhang B, Deng K, Bottle S, Zhu H (2017) Selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid using O2 and a photocatalyst of Co-thioporphyrazine bonded to g-C3N4. J Am Chem Soc 139(41):14775–14782. https://doi.org/10.1021/jacs.7b08861
Yan D, Wang G, Gao K, Lu X, **n J, Zhang S (2018) One-pot synthesis of 2,5-furandicarboxylic acid from fructose in ionic liquids. Ind Eng Chem Res 57(6):1851–1858. https://doi.org/10.1021/acs.iecr.7b04947
Yang C-F, Huang C-R (2016) Biotransformation of 5-hydroxy-methylfurfural into 2,5-furan-dicarboxylic acid by bacterial isolate using thermal acid algal hydrolysate. Bioresour Technol 214:311–318. https://doi.org/10.1016/j.biortech.2016.04.122
Yang C-F, Huang C-R (2018) Isolation of 5-hydroxymethylfurfural biotransforming bacteria to produce 2,5-furan dicarboxylic acid in algal acid hydrolysate. J Biosci Bioeng 125(4):407–412. https://doi.org/10.1016/j.jbiosc.2017.11.005
Yang D-D, François JM, de Billerbeck GM (2012) Cloning, expression and characterization of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium strain BKM-F-1767. BMC Microbiol 12(1):126. https://doi.org/10.1186/1471-2180-12-126
Yee KL, Jansen LE, Lajoie CA, Penner MH, Morse L, Kelly CJ (2018) Furfural and 5-hydroxymethyl-furfural degradation using recombinant manganese peroxidase. Enzym Microb Technol 108:59–65. https://doi.org/10.1016/j.enzmictec.2017.08.009
Yu J, Stahl H (2008) Microbial utilization and biopolyester synthesis of bagasse hydrolysates. Bioresour Technol 99(17):8042–8048. https://doi.org/10.1016/j.biortech.2008.03.071
Yuan H, Li J, Shin H-D, Du G, Chen J, Shi Z, Liu L (2018a) Improved production of 2,5-furandicarboxylic acid by overexpression of 5-hydroxymethylfurfural oxidase and 5-hydroxymethylfurfural/furfural oxidoreductase in Raoultella ornithinolytica BF60. Bioresour Technol 247(Supplement C):1184–1188. https://doi.org/10.1016/j.biortech.2017.08.166
Yuan H, Liu Y, Li J, Shin H-d DG, Shi Z, Chen J, Liu L (2018b) Combinatorial synthetic pathway fine-tuning and comparative transcriptomics for metabolic engineering of Raoultella ornithinolytica BF60 to efficiently synthesize 2,5-furandicarboxylic acid. Biotechnol Bioeng 115(9):2148–2155. https://doi.org/10.1002/bit.26725
Yuan H, Liu Y, Lv X, Li J, Du G, Shi Z, Liu L (2018c) Enhanced 2, 5-furandicarboxylic acid (FDCA) production in Raoultella ornithinolytica BF60 by manipulation of the key genes in FDCA biosynthesis pathway. J Microbiol Biotechnol 28(12):1999–2008. https://doi.org/10.4014/jmb.1808.8057
Zaldivar J, Martinez A, Ingram LO (1999) Effect of selected aldehydes on the growth and fermentation of ethanologenic Escherichia coli. Biotechnol Bioeng 65(1):24–33. https://doi.org/10.1002/(sici)1097-0290(19991005)65:1<24::aid-bit4>3.0.co;2-2
Zdzienicka M, Tudek B, Zieleńska M, Szymczyk T (1978) Mutagenic activity of furfural in Salmonella typhimurium TA100. Mutat Res/Genet Toxicol 58(2):205–209. https://doi.org/10.1016/0165-1218(78)90010-1
Zhang Z, Deng K (2015) Recent advances in the catalytic synthesis of 2,5-furandicarboxylic acid and its derivatives. ACS Catal 5(11):6529–6544. https://doi.org/10.1021/acscatal.5b01491
Zhang Y, Ezeji TC (2013) Transcriptional analysis of Clostridium beijerinckii NCIMB 8052 to elucidate role of furfural stress during acetone butanol ethanol fermentation. Biotechnol Biofuels 6(1):66. https://doi.org/10.1186/1754-6834-6-66
Zhang Z, Huber GW (2018) Catalytic oxidation of carbohydrates into organic acids and furan chemicals. Chem Soc Rev 47(4):1351–1390. https://doi.org/10.1039/C7CS00213K
Zhang J, Zhu Z, Wang X, Wang N, Wang W, Bao J (2010) Biodetoxification of toxins generated from lignocellulose pretreatment using a newly isolated fungus, Amorphotheca resinae ZN1, and the consequent ethanol fermentation. Biotechnol Biofuels 3(1):26. https://doi.org/10.1186/1754-6834-3-26
Zhang Y, Han B, Ezeji TC (2012) Biotransformation of furfural and 5-hydroxymethyl furfural (HMF) by Clostridium acetobutylicum ATCC 824 during butanol fermentation. New Biotechnol 29(3):345–351. https://doi.org/10.1016/j.nbt.2011.09.001
Zhang D, Ong YL, Li Z, Wu JC (2013) Biological detoxification of furfural and 5-hydroxyl methyl furfural in hydrolysate of oil palm empty fruit bunch by Enterobacter sp. FDS8. Biochem Eng J 72:77–82. https://doi.org/10.1016/j.bej.2013.01.003
Zhang S, Lan J, Chen Z, Yin G, Li G (2017a) Catalytic synthesis of 2,5-furandicarboxylic acid from furoic acid: transformation from C5 platform to C6 derivatives in biomass utilizations. ACS Sustain Chem Eng 5(10):9360–9369. https://doi.org/10.1021/acssuschemeng.7b02396
Zhang X-Y, Zong M-H, Li N (2017b) Whole-cell biocatalytic selective oxidation of 5-hydroxymethylfurfural to 5-hydroxymethyl-2-furancarboxylic acid. Green Chem 19(19):4544–4551. https://doi.org/10.1039/C7GC01751K
Zhou X, Zhou X, Xu Y, Chen RR (2017) Gluconobacter oxydans (ATCC 621H) catalyzed oxidation of furfural for detoxification of furfural and bioproduction of furoic acid. J Chem Technol Biotechnol 92(6):1285–1289. https://doi.org/10.1002/jctb.5122
Zhou H, Xu H, Wang X, Liu Y (2019) Convergent production of 2,5-furandicarboxylic acid from biomass and CO2. Green Chem 21(11):2923–2927. https://doi.org/10.1039/C9GC00869A
Zhu H, Cao Q, Li C, Mu X (2011) Acidic resin-catalysed conversion of fructose into furan derivatives in low boiling point solvents. Carbohydr Res 346(13):2016–2018. https://doi.org/10.1016/j.carres.2011.05.026
Funding
This work was supported by the National Natural Science Foundation of China (31501413); Shandong Key Project of Research & Development Plan (2017GSF221019); State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology, Shandong Academy of Sciences (ZZ20190314); Young Doctorate Cooperation Fund Project, QiLu University of Technology (Shandong Academy of Sciences) (2017BSHZ021); Natural Science Foundation of Shandong Province (ZR2017BC072, ZR2019PC060); A Project of Shandong Province Higher Educational Science and Technology Program (A18KA116); and The Dragon City Excellent Researcher Award Program from Zhucheng and Taishan Industry Leading Talents Program.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no competing interests.
Ethical approval
This article does not contain any studies with human participants or animals performed by any of the authors.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Yuan, H., Liu, H., Du, J. et al. Biocatalytic production of 2,5-furandicarboxylic acid: recent advances and future perspectives. Appl Microbiol Biotechnol 104, 527–543 (2020). https://doi.org/10.1007/s00253-019-10272-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00253-019-10272-9