Industrial production, application, microbial biosynthesis and degradation of furanic compound, hydroxymethylfurfural (HMF)
Open accessAbstract
Biorefinery is increasingly embraced as an environmentally friendly approach that has the potential to shift current petroleum-based chemical and material manufacture to renewable sources. Furanic compounds, particularly hydroxymethylfurfurals (HMFs) are platform chemicals, from which a variety of value-added chemicals can be derived. Their biomanufacture and biodegradation therefore will have a large impact. Here, we first review the potential industrial production of 4-HMF and 5-HMF, then we summarize the known microbial biosynthesis and biodegradation pathways of furanic compounds with emphasis on the enzymes in each pathway. We especially focus on the structure, function and catalytic mechanism of MfnB (4-(hydroxymethyl)-2-furancarboxyaldehyde-phosphate synthase) and hmfH (HMF oxidase), which catalyze the formation of phosphorylated 4-HMF and the oxidation of 5-HMF to furandicarboxylic acid (2,5-FDCA), respectively. Understanding the structure-function relationship of these enzymes will provide important insights in enzyme engineering, which eventually will find industry applications in mass-production of biobased polymers and other bulk chemicals in future.
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HMF is a key biomass platform intermediate that is commonly obtained from glucose or fructose by dehydration reactions.
“HMF is a key biomass platform intermediate that is commonly obtained from glucose or fructose by dehydration reactions.”
From Biorefineries: Achievements and challenges for a bio-based economy (2022) · cites this paper as Wang et al., 2018
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Bozell, J. J., & Petersen, G. R. (2010) · Green Chemistry · doi:10.1039/b922014c · Cited by 4,566 · cited 2× · see citing works
“This list evaluated chemicals based on a set of criteria including properties like the compound receiving attention in literature, the compound having strong potential as a platform, and the product’s ability to serve as a building block of biorefinery [1].”
BackgroundHydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources
van Putten, R.-J., van der Waal, J. C., de Jong, E., Rasrendra, C. B., Heeres, H. J., & de Vries, J. G. (2013) · Chemical Reviews · doi:10.1021/cr300182k · Cited by 2,886 · cited 4× · see citing works
“Synthesis and application of 5-HMF (left) [5,7] and 4-HMF (right) [6].”
BackgroundInfluentialFermentation of lignocellulosic hydrolysates. II: inhibitors and mechanisms of inhibition
Palmqvist, E. A., & Hahn‐Hägerdal, B. (2000) · Bioresource Technology · doi:10.1016/s0960-8524(99)00161-3 · Cited by 2,526 · cited 1× · see citing works
“coli) and Saccharomyces cerevisiae strains [46,47].”
Rosatella, A. A., Simeonov, S. P., Frade, R. F. M., & Afonso, C. A. M. (2011) · Green Chemistry · doi:10.1039/c0gc00401d · Cited by 1,655 · cited 2× · see citing works
“Synthesis and application of 5-HMF (left) [5,7] and 4-HMF (right) [6].”
BackgroundFermentation of lignocellulosic hydrolysates. I: inhibition and detoxification
Palmqvist, E. A., & Hahn‐Hägerdal, B. (2000) · Bioresource Technology · doi:10.1016/s0960-8524(99)00160-1 · Cited by 1,370 · see citing works
Burgess, S. K., Leisen, J., Kraftschik, B. E., Mubarak, C. R., Kriegel, R. M., & Koros, W. J. (2014) · Macromolecules · doi:10.1021/ma5000199 · Cited by 651 · see citing works
Nicolaou, S. A., Gaida, S. M., & Papoutsakis, E. T. (2010) · Metabolic Engineering · doi:10.1016/j.ymben.2010.03.004 · Cited by 537 · see citing works
Advances in 5-hydroxymethylfurfural production from biomass in biphasic solvents
Saha, B., & Abu‐Omar, M. M. (2013) · Green Chemistry · doi:10.1039/c3gc41324a · Cited by 527 · cited 1× · see citing works
“Currently, most 5-HMFs are obtained from multiple step dehydration reactions of furanoses, which are derived from pretreatment and hydrolysis of cellulose and hemicellulose polymers [28].”
BackgroundMukherjee, A., Dumont, M., & Raghavan, V. (2014) · Biomass and Bioenergy · doi:10.1016/j.biombioe.2014.11.007 · Cited by 510 · cited 1× · see citing works
“The steps in the process of pretreating biomass substrates include using homogeneous mineral acid, Brønsted acidic ionic liquids (IL), Lewis acidic metal halides and recyclable heterogeneous catalysts in pure organic or aqueous solvents [29,30] (Figure 1, left).”
MethodYu, I. K. M., & Tsang, D. C. W. (2017) · Bioresource Technology · doi:10.1016/j.biortech.2017.04.026 · Cited by 497 · see citing works
Modig, T., Lidén, G., & Taherzadeh, M. J. (2002) · Biochemical Journal · doi:10.1042/0264-6021:3630769 · Cited by 361 · see citing works
Furandicarboxylic Acid (FDCA), A Versatile Building Block for a Very Interesting Class of Polyesters
de Jong, E., Dam, M. A., Sipos, L., & Gruter, G.-J. M. (2012) · ACS Symposium Series · doi:10.1021/bk-2012-1105.ch001 · Cited by 344 · cited 1× · see citing works
“Since hmfH catalyzes the oxidation of 5-HMF to 2,5-FDCA, which can be esterified to form polymers with a wide range of application [67].”
BackgroundModig, T., Lidén, G., & Taherzadeh, M. J. (2002) · Biochemical Journal · doi:10.1042/bj3630769 · Cited by 319 · see citing works
Papageorgiou, G. Z., Tsanaktsis, V., & Bikiaris, D. Ν. (2014) · Physical Chemistry Chemical Physics · doi:10.1039/c4cp00518j · Cited by 314 · see citing works
Enzyme‐Catalyzed Oxidation of 5‐Hydroxymethylfurfural to Furan‐2,5‐dicarboxylic Acid
Dijkman, W. P., Groothuis, D. E., & Fraaije, M. W. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201402904 · Cited by 303 · see citing works
Upgrading Furfurals to Drop-in Biofuels: An Overview
Bohre, A., Dutta, S., Saha, B., & Abu‐Omar, M. M. (2015) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.5b00271 · Cited by 302 · cited 2× · see citing works
“2,5-DMF stands out as an alternative biofuel due to its high octane number, high energy density, higher boiling point, lower water miscibility and lower volatility, which makes it a potential drop-in replacement to both gasoline and diesel [10,11].”
BackgroundObservation of Covalent Intermediates in an Enzyme Mechanism at Atomic Resolution
Heine, A., DeSantis, G., Luz, J. G., Mitchell, M. L., Wong, C., & Wilson, I. A. (2001) · Science · doi:10.1126/science.1063601 · Cited by 281 · cited 2× · see citing works
“At the active site, two lysines and two aspartic acids are strictly conserved in both the MfnB and deoxyribose-5-phosphate aldolase (DERA, a class I aldolase) active site and are essential in the function of MfnB and DERA [45].”
BackgroundKoopman, F. W., Wierckx, N. J. P., de Winde, J. H., & Ruijssenaars, H. J. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0913039107 · Cited by 275 · cited 5× · see citing works
“The hmfFGH gene cluster involved in the metabolism of HMF has also been elucidated [63].”
BackgroundInfluentialCombustion and Emissions of 2,5-Dimethylfuran in a Direct-Injection Spark-Ignition Engine
Zhong, S., Daniel, R., Xu, H., Zhang, J., Turner, D., WYSZYNSKI, M. L., & Richards, P. (2010) · Energy & Fuels · doi:10.1021/ef901575a · Cited by 270 · cited 1× · see citing works
“Studies have also shown that the combustion and emission properties of 2,5-DMF are comparable to that of commercial gasoline [12,13].”
BackgroundBiomass to Furanics: Renewable Routes to Chemicals and Fuels
Caes, B. R., Teixeira, R. E., Knapp, K. G., & Raines, R. T. (2015) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.5b00473 · Cited by 248 · cited 2× · see citing works
“2,5-DMF stands out as an alternative biofuel due to its high octane number, high energy density, higher boiling point, lower water miscibility and lower volatility, which makes it a potential drop-in replacement to both gasoline and diesel [10,11].”
BackgroundLiu, Z. L., Moon, J., Andersh, B. J., Slininger, P. J., & Weber, S. A. (2008) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-008-1702-0 · Cited by 244 · see citing works
Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates
López, M. J., Nichols, N. N., Dien, B. S., Moreno, J., & Bothast, R. J. (2004) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-003-1401-9 · Cited by 228 · see citing works
Zhang, J., Zhu, Z., Wang, X., Wang, N., Wang, W., & Bao, J. (2010) · Biotechnology for Biofuels · doi:10.1186/1754-6834-3-26 · Cited by 190 · see citing works
Analysis of 5‐hydroxymethylfurfual in coffee, dried fruits and urine
Murkovic, M., & Pichler, N. (2006) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.200500262 · Cited by 182 · cited 1× · see citing works
“highly acidic environment during roasting supporting the idea the HMF is not naturally present in coffee but is instead a byproduct of the thermal processing [27].”
BackgroundMolecular architecture of rabbit skeletal muscle aldolase at 2.7-A resolution.
SYGUSCH, J., Beaudry, D., & Allaire, M. (1987) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.84.22.7846 · Cited by 176 · see citing works
Microbial degradation of furanic compounds: biochemistry, genetics, and impact
Wierckx, N. J. P., Koopman, F. W., Ruijssenaars, H. J., & de Winde, J. H. (2011) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-011-3632-5 · Cited by 176 · cited 7× · see citing works
“In addition to two gene clusters, additional genes might also be involved in degradation of HMF or furfural [57].”
BackgroundInfluentialKowalski, S., Łukasiewicz, M., Duda‐Chodak, A., & Zięć, G. (2013) · Polish Journal of Food and Nutrition Sciences · doi:10.2478/v10222-012-0082-4 · Cited by 166 · cited 2× · see citing works
“HMF occurs naturally during the processing of many different foods including coffee, cereals, and vegetable products [25].”
BackgroundDijkman, W. P., & Fraaije, M. W. (2013) · Applied and Environmental Microbiology · doi:10.1128/aem.03740-13 · Cited by 163 · cited 2× · see citing works
“The N-terminal GMC domain (Pfam 00732) is involved in binding of FAD, whereas the second conserved domain C-terminal GMC (Pfam 05199) contains a strictly conserved histidine (H467) [65,66].”
BackgroundCorre, C., Song, L., O'Rourke, S., Chater, K. F., & Challis, G. L. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0805530105 · Cited by 155 · cited 3× · see citing works
“In the proposed biosynthetic pathway, MmfL catalyzes the condensation of dihydroxyacetone phosphate and a β-ketoacyl-thioester intermediate in fatty acid biosynthesis likely through the butenolide intermediate, which then undergoes dephosphorylation, cyclization and dehydration reactions, likely catalyzed by MmfP and…”
Backgroundde Almeida, J. R. M., Röder, A., Modig, T., Laadan, B., Lidén, G., & Gorwa‐Grauslund, M. F. (2008) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-008-1364-y · Cited by 146 · cited 1× · see citing works
“coli) and Saccharomyces cerevisiae strains [46,47].”
Rout, P. K., Nannaware, A. D., Prakash, O., Kalra, A., & Rajasekharan, R. (2015) · Chemical Engineering Science · doi:10.1016/j.ces.2015.12.002 · Cited by 135 · cited 1× · see citing works
“The steps in the process of pretreating biomass substrates include using homogeneous mineral acid, Brønsted acidic ionic liquids (IL), Lewis acidic metal halides and recyclable heterogeneous catalysts in pure organic or aqueous solvents [29,30] (Figure 1, left).”
MethodAdvances in polymer precursors and bio‐based polymers synthesized from 5‐hydroxymethylfurfural
Zhang, D., & Dumont, M. (2017) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.28527 · Cited by 133 · cited 3× · see citing works
“4-HMF could be upgraded into other valuable platform compounds such as 2,4-bis(hydroxymethyl)furan (2,4-BHF) (the precursor of calcineurin inhibitor [21]), 4-(hydroxymethyl)furan-2-carboxylic acid (4-HMF-2-CA) (which could convert to prostaglandin receptor EP4 [22]), furan-2,4-dicarboxylic acid (2,4-FDCA) (which could…”
BackgroundStructure-Based Enzyme Tailoring of 5-Hydroxymethylfurfural Oxidase
Dijkman, W. P., Binda, C., Fraaije, M. W., & Mattevi, A. (2015) · ACS Catalysis · doi:10.1021/acscatal.5b00031 · Cited by 118 · cited 5× · see citing works
“The crystal structure of hmfH exhibited the similar structural architecture with two globular domains (a FAD-binding domain and a smaller cap domain), as other GMC members [66].”
BackgroundInfluentialMurkovic, M., & Bornik, M. (2007) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.200600251 · Cited by 117 · cited 1× · see citing works
“Furans are found at very low levels in groups of food that are rich in carbohydrates which contain hexoses that can be easily dehydrated to HMF [26], or amino acids which can react to form a Schiff base that further reacts to form HMF [25].”
BackgroundThe three-dimensional structure of N -acetylneuraminate lyase from Escherichia coli
Izard, T., Lawrence, M. C., Malby, R. L., Lilley, G. G., & Colman, P. M. (1994) · Structure · doi:10.1016/s0969-2126(00)00038-1 · Cited by 116 · see citing works
Kim, C.-G., Yu, T., Fryhle, C. B., Handa, S., & Floss, H. G. (1998) · Journal of Biological Chemistry · doi:10.1074/jbc.273.11.6030 · Cited by 111 · see citing works
Wang, X., Miller, E. N., Yomano, L. P., Zhang, X., Shanmugam, K. T., & Ingram, L. O. (2011) · Applied and Environmental Microbiology · doi:10.1128/aem.05008-11 · Cited by 100 · see citing works
Codou, A., Moncel, M., van Berkel, J. G., Guigo, N., & Sbirrazzuoli, N. (2016) · Physical Chemistry Chemical Physics · doi:10.1039/c6cp01227b · Cited by 100 · see citing works
Factors influencing the stabilities of nematic liquid crystals
Dewar, M. J. S., & Riddle, R. M. (1975) · Journal of the American Chemical Society · doi:10.1021/ja00856a010 · Cited by 100 · cited 1× · see citing works
“4-HMF could be upgraded into other valuable platform compounds such as 2,4-bis(hydroxymethyl)furan (2,4-BHF) (the precursor of calcineurin inhibitor [21]), 4-(hydroxymethyl)furan-2-carboxylic acid (4-HMF-2-CA) (which could convert to prostaglandin receptor EP4 [22]), furan-2,4-dicarboxylic acid (2,4-FDCA) (which could…”
BackgroundProduct binding and role of the C-terminal region in Class I D-fructose 1, 6-bisphosphate aldolase
Blom, N. S., & SYGUSCH, J. (1997) · Nature Structural & Molecular Biology · doi:10.1038/nsb0197-36 · Cited by 94 · see citing works
Thiyagarajan, S., Pukin, A. V., van Haveren, J., Lutz, M., & van Es, D. S. (2013) · RSC Advances · doi:10.1039/c3ra42457j · Cited by 84 · cited 1× · see citing works
“Due to the complexities and difficulties of synthesis, 2,4-substituted furans were fairly expensive compounds [31].”
BackgroundTerzopoulou, Z. N., Tsanaktsis, V., Nerantzaki, M., Achilias, D. S., Vaimakis, T., Papageorgiou, G. Z., & Bikiaris, D. Ν. (2015) · Journal of Analytical and Applied Pyrolysis · doi:10.1016/j.jaap.2015.11.016 · Cited by 84 · see citing works
Effects of furfural on anaerobic continuous cultivation of Saccharomyces cerevisiae
Horváth, I. S., Taherzadeh, M. J., Niklasson, C., & Lidén, G. (2001) · Biotechnology and Bioengineering · doi:10.1002/bit.10090 · Cited by 81 · see citing works
Kim, H., Certa, U., Döbeli, H., Jakob, P., & Hol, W. G. J. (1998) · Biochemistry · doi:10.1021/bi972233h · Cited by 74 · see citing works
Hester, G., Brenner‐Holzach, O., Rossi, F. A., Struck-Donatz, M., Winterhalter, K. H., Smit, J., & Piontek, K. (1991) · FEBS Letters · doi:10.1016/0014-5793(91)80875-4 · Cited by 73 · see citing works
Barciszewski, J., Siboska, G. E., Pedersen, B. O., Clark, B. F. C., & Rattan, S. I. S. (1997) · FEBS Letters · doi:10.1016/s0014-5793(97)01037-5 · Cited by 71 · see citing works
Jia, J., Lindqvist, Y., Schneider, G., Schörken, U., & Sprenger, G. A. (1997) · Protein Science · doi:10.1002/pro.5560060113 · Cited by 71 · see citing works
Engineering Sugar Utilization and Microbial Tolerance toward Lignocellulose Conversion
Nieves, L. M., Panyon, L. A., & Wang, X. (2015) · Frontiers in Bioengineering and Biotechnology · doi:10.3389/fbioe.2015.00017 · Cited by 67 · cited 1× · see citing works
“coli resistant to furfural and HMF [56].”
Qin, Y., Zong, M., Lou, W., & Li, N. (2016) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.6b00996 · Cited by 66 · cited 1× · see citing works
“5-HMF as an intermediate molecule is important because it can be transformed through simple chemical reactions into a large number of useful compounds [5,7,9] (Figure 1, left).”
BackgroundBaba, Y., Hirukawa, N., Tanohira, N., & Sodeoka, M. (2003) · Journal of the American Chemical Society · doi:10.1021/ja034694y · Cited by 63 · cited 1× · see citing works
“4-HMF could be upgraded into other valuable platform compounds such as 2,4-bis(hydroxymethyl)furan (2,4-BHF) (the precursor of calcineurin inhibitor [21]), 4-(hydroxymethyl)furan-2-carboxylic acid (4-HMF-2-CA) (which could convert to prostaglandin receptor EP4 [22]), furan-2,4-dicarboxylic acid (2,4-FDCA) (which could…”
BackgroundBoopathy, R., & Daniels, L. (1991) · Current Microbiology · doi:10.1007/bf02104134 · Cited by 59 · cited 1× · see citing works
“For example, three fungal [58–60] and two anaerobic microorganisms [61,62] have been reported to degrade furanic aldehyde as well.”
BackgroundGrowth of a Strictly Anaerobic Bacterium on Furfural (2-Furaldehyde)
Brune, G., Schoberth, S. M., & Sahm, H. (1983) · Applied and Environmental Microbiology · doi:10.1128/aem.46.5.1187-1192.1983 · Cited by 55 · cited 1× · see citing works
“For example, three fungal [58–60] and two anaerobic microorganisms [61,62] have been reported to degrade furanic aldehyde as well.”
BackgroundDimitriadis, T., Bikiaris, D. Ν., Papageorgiou, G. Z., & Floudas, G. A. (2016) · Macromolecular Chemistry and Physics · doi:10.1002/macp.201600278 · Cited by 48 · see citing works
Linked strategy for the production of fuels via formose reaction
Deng, J. G., Pan, T., Xu, Q., Chen, M., Zhang, Y., Guo, Q., & Fu, Y. (2013) · Scientific Reports · doi:10.1038/srep01244 · Cited by 40 · cited 3× · see citing works
“4-HMF can also be employed as a precursor molecule to produce 2,4-DMF or branched-chain alkanes as liquid transportation fuels [4].”
BackgroundGamma-Butyrolactone and Furan Signaling Systems in Streptomyces
Sidda, J. D., & Corre, C. (2012) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/b978-0-12-404634-4.00004-8 · Cited by 34 · cited 3× · see citing works
“In the proposed biosynthetic pathway, MmfL catalyzes the condensation of dihydroxyacetone phosphate and a β-ketoacyl-thioester intermediate in fatty acid biosynthesis likely through the butenolide intermediate, which then undergoes dephosphorylation, cyclization and dehydration reactions, likely catalyzed by MmfP and…”
BackgroundSynthesis and kinetic modeling of biomass‐derived renewable polyesters
Lomelí‐Rodríguez, M., Martín‐Molina, M., Jiménez‐Pardo, M., Nasim‐Afzal, Z., Cauët, S. I., Davies, T. E., Rivera‐Toledo, M., & López-Sánchez, J. A. (2016) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.28173 · Cited by 32 · see citing works
Interaction between 2,5-Dimethylfuran and Nitric Oxide: Experimental and Modeling Study
Alexandrino, K., Millera, Á., Bilbao, R., & Alzueta, M. U. (2014) · Energy & Fuels · doi:10.1021/ef5005573 · Cited by 24 · cited 1× · see citing works
“Studies have also shown that the combustion and emission properties of 2,5-DMF are comparable to that of commercial gasoline [12,13].”
BackgroundThermally Treated Grass Fibers as Colonizable Substrate for Beneficial Bacterial Inoculum
Trifonova, R., Postma, J., Ketelaars, J. J. M. H., & van Elsas, J. D. (2008) · Microbial Ecology · doi:10.1007/s00248-008-9376-9 · Cited by 21 · see citing works
Cui, M., Deng, J. G., Li, X., & Fu, Y. (2016) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.5b01657 · Cited by 21 · cited 8× · see citing works
“The subsequent product ketohexoses are then converted to 4-HMF through an acid-catalyzed dehydration [6] (Figure 1, right).”
BackgroundMethodInfluentialRenewable Green Platform Chemicals for Polymers
Ray, P., Smith, C., Simon, G. P., & Saito, K. (2017) · Molecules · doi:10.3390/molecules22030376 · Cited by 21 · cited 3× · see citing works
“4-HMF could be upgraded into other valuable platform compounds such as 2,4-bis(hydroxymethyl)furan (2,4-BHF) (the precursor of calcineurin inhibitor [21]), 4-(hydroxymethyl)furan-2-carboxylic acid (4-HMF-2-CA) (which could convert to prostaglandin receptor EP4 [22]), furan-2,4-dicarboxylic acid (2,4-FDCA) (which could…”
BackgroundWang, Y. U., Xu, H., Jones, M. K., & White, R. H. (2015) · Journal of Bacteriology · doi:10.1128/jb.00401-15 · Cited by 16 · cited 1× · see citing works
“MfnB catalyzes the formation of 4-hydroxymethylfurfural phosphate (4-HMF-P) from two molecules of D-glyceraldehyde-3phosphate (GA-3P) in the biosynthetic pathway to the furan moiety of the coenzyme methanofuran found in methanogens (Figure 3) [36].”
BackgroundBiosynthesis of the 5-(Aminomethyl)-3-furanmethanol Moiety of Methanofuran
Miller, D., Wang, Y. U., Xu, H., Harich, K. C., & White, R. H. (2014) · Biochemistry · doi:10.1021/bi500615p · Cited by 16 · cited 2× · see citing works
“Another example is a novel enzyme, 4-(hydroxymethyl)-2-furancarboxyaldehyde-phosphate synthase (MfnB) [34,35].”
BackgroundBrief Review of Liquid Crystals
Ermakov, S. F., Белецкий, А. В., Эйсмонт, О. Л., & Николаев, В. И. (2015) · Biological and medical physics, biomedical engineering · doi:10.1007/978-3-319-20349-2_2 · Cited by 14 · see citing works
Wang, Y. U., Jones, M. K., Xu, H., Ray, W. K., & White, R. H. (2015) · Biochemistry · doi:10.1021/acs.biochem.5b00176 · Cited by 11 · cited 7× · see citing works
“MfnB catalyzed reaction and the structure of methanofuran [34,35].”
BackgroundInfluentialBobik, T. A., Morales, E. J., Shin, A., Cascio, D., Sawaya, M. R., Arbing, M. A., Yeates, T. O., & Rasche, M. E. (2014) · Acta Crystallographica Section F Structural Biology Communications · doi:10.1107/s2053230x1402130x · Cited by 3 · see citing works
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Sajid, M., Zhao, X., & Liu, D. (2018) · Green Chemistry · doi:10.1039/c8gc02680g · Cited by 727 · see citing works
Cell wall hemicellulose for sustainable industrial utilization
Qaseem, M. F., Shaheen, H., & Wu, A. (2021) · Renewable and Sustainable Energy Reviews · doi:10.1016/j.rser.2021.110996 · Cited by 229 · see citing works
Biorefineries: Achievements and challenges for a bio-based economy
Calvo-Flores, F. G., & Martin-Martinez, F. J. (2022) · Frontiers in Chemistry · doi:10.3389/fchem.2022.973417 · Cited by 176 · see citing works
Castiello, C., Junghanns, P., Mergel, A. M., Jacob, C., Ducho, C., Valente, S., Rotili, D., Fioravanti, R., Zwergel, C., & Mai, A. (2023) · Green Chemistry · doi:10.1039/d2gc03772f · Cited by 159 · see citing works
Advances in Electrochemical Modification Strategies of 5‐Hydroxymethylfurfural
Simoska, O., Rhodes, Z., Weliwatte, N. S., Cabrera‐Pardo, J. R., Gaffney, E. M., Lim, K., & Minteer, S. D. (2021) · ChemSusChem · doi:10.1002/cssc.202100139 · Cited by 97 · see citing works
Expanding the anaerobic digestion map: A review of intermediates in the digestion of food waste
Hunter, S. M., Blanco, E., & Borrion, A. L. (2020) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2020.144265 · Cited by 67 · see citing works
“Methanobacterium, Methanococcus, Methanobrevibacter, Methanomicrobium, Methanosarcina and Methanoseata are reported as being the dominant methanogens (P. Wang et al., 2018).”
BackgroundJiju, P. S., Patel, A. K., Shruthy, N. S., Shalu, S., Dong, C.-D., & Singhania, R. R. (2025) · Bioresources and Bioprocessing · doi:10.1186/s40643-025-00929-x · Cited by 61 · see citing works
“Traditionally burned for energy in pulp, paper, and biofuel industries, lignin is now being explored for high-value applications due to its abundance (15–30% of plant biomass) and structural complexity (Sun and Peng 2023; Wang et al. 2018).”
Vikanova, K., Редина, Е. А., Kapustin, G. I., Chernova, M. S., Tkachenko, O. P., Nissenbaum, V. D., & Kustov, L. M. (2021) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.0c06560 · Cited by 52 · see citing works
Enzymatic reactions towards aldehydes: An overview
Schober, L., Dobiašová, H., Jurkaš, V., Parmeggiani, F., Rudroff, F., & Winkler, M. (2023) · Flavour and Fragrance Journal · doi:10.1002/ffj.3739 · Cited by 51 · see citing works
“232 Furthermore, oxidation of HMF by AOx was discussed in Section 2.3.1.”
MethodInfluentialAğçam, E. (2022) · Food Analytical Methods · doi:10.1007/s12161-021-02214-x · Cited by 42 · see citing works
Maitra, S., & Singh, V. (2022) · Journal of Cleaner Production · doi:10.1016/j.jclepro.2022.134383 · Cited by 31 · see citing works
Blanco, J., Martín, S., Linares, M., Iglesias, J., & Moreno, J. (2023) · Journal of Cleaner Production · doi:10.1016/j.jclepro.2023.137513 · Cited by 31 · see citing works
Acid hydrolysis conditions for the production of fine chemicals from Gracilaria birdiae alga biomass
Albuquerque, J. C. S., Araújo, M. L. H., Rocha, M. V. P., de Souza, B. W. S., de Castro, G. M. C., Cordeiro, E. M. S., Silva, J. D. S., & Benevídes, N. M. B. (2020) · Algal Research · doi:10.1016/j.algal.2020.102139 · Cited by 29 · see citing works
A bacterial biosynthetic pathway for methylated furan fatty acids
Lemke, R. A. S., Olson, S. M., Morse, K., Karlen, S. D., Higbee, A. J., Beebe, E. T., Ralph, J., Coon, J. J., Fox, B. G., & Donohue, T. J. (2020) · Journal of Biological Chemistry · doi:10.1074/jbc.ra120.013697 · Cited by 28 · see citing works
da Silva, L. C., Viganó, J., Sanches, V. L., Mesquita, L. M. D. S., Pizani, R. S., & Rostagno, M. A. (2022) · Food Chemistry · doi:10.1016/j.foodchem.2022.135117 · Cited by 27 · see citing works
Molinaro, J. M., Swartzentruber, J., Ledger, V. W., Fredericks, Z. T., Alonso, D. M., & Wettstein, S. G. (2025) · EES Catalysis · doi:10.1039/d5ey00028a · Cited by 22 · see citing works
Hahn, T., Torkler, S., van der Bolt, R., Gammel, N., Hesse, M., Möller, A., Preylowski, B., Hubracht, V., Patzsch, K., & Zibek, S. (2020) · Process Biochemistry · doi:10.1016/j.procbio.2020.04.011 · Cited by 22 · see citing works
Kasmi, N., Terzopoulou, Z. N., Chebbi, Y., Dieden, R. A., Habibi, Y., & Bikiaris, D. Ν. (2021) · Polymer Degradation and Stability · doi:10.1016/j.polymdegradstab.2021.109804 · Cited by 20 · see citing works
Hammoud, M., Hmadeh, M., & Ahmad, M. N. (2024) · Applied Materials Today · doi:10.1016/j.apmt.2024.102359 · Cited by 19 · see citing works
Omodolor, I. S., Kalidindi, S., Walz, S. A., Coleman, M. R., Gogar, R., Viamajala, S., Granados, M. L., & Alba‐Rubio, A. C. (2022) · Catalysis Science & Technology · doi:10.1039/d2cy01619b · Cited by 17 · see citing works
Donoso, R. A., González-Toro, F., & Pérez-Pantoja, D. R. (2021) · Computational and Structural Biotechnology Journal · doi:10.1016/j.csbj.2021.04.017 · Cited by 16 · see citing works
Huang, M., Li, T., Hardie, W. J., Tang, W., & Li, X. (2022) · Flavour and Fragrance Journal · doi:10.1002/ffj.3694 · Cited by 15 · see citing works
Autochthonous microbes and their key properties in browning reduction during soy sauce fermentation
Det-udom, R., Prakitchaiwattana, C., & Mahawanich, T. (2019) · LWT · doi:10.1016/j.lwt.2019.05.042 · Cited by 15 · see citing works
BRAGA, M. G. A. D. M., Ferreira, P. M., & de Almeida, J. R. M. (2020) · Biofuels Bioproducts and Biorefining · doi:10.1002/bbb.2156 · Cited by 15 · see citing works
Bishop, B. D. C., Sanusi, I. A., & Kana, G. E. B. (2024) · Biomass Conversion and Biorefinery · doi:10.1007/s13399-024-06127-7 · Cited by 14 · see citing works
“The presence of these inhibitors within the fermentation media inhibits microbial growth through DNA damage via fragmentation, inhibition of enzymes within the glycolytic pathway, and the reduction of NADPH available for microorganism metabolism [14].”
Huertas-Alonso, A. J., Gavahian, M., González-Serrano, D. J., Hadidi, M., Salgado-Ramos, M., Sánchez‐Verdú, P., Simirgiotis, M. J., Barba, F. J., Franco, D., Lorenzo, J. M., et al. (2021) · Antioxidants · doi:10.3390/antiox10111652 · Cited by 14 · see citing works
“These chemicals possess the capability of generating multiple and interesting products on an industrial level, such as biofuels, solvents, monomers, or pesticides [20,21].”
BackgroundBioconversion of Agricultural Residue into Biofuel and High-Value Biochemicals: Recent Advancement
Rose, P. K. (2022) · Energy, environment, and sustainability · doi:10.1007/978-981-16-8682-5_9 · Cited by 14 · see citing works
A rigid plant oil-based thermoset with a furfural-derived cyclobutane cross-linker
Tellers, J., Sbirrazzuoli, N., & Guigo, N. (2021) · Green Chemistry · doi:10.1039/d0gc04323k · Cited by 13 · see citing works
Baruah, J., Medhi, U., Nath, B. K., Deka, R. C., & Kalita, E. (2025) · Next Energy · doi:10.1016/j.nxener.2025.100420 · Cited by 13 · see citing works
Glucose dehydration reaction over metal halides supported on activated charcoal catalysts
Martín, G. D., Lara, B., Bounoukta, C. E., Domínguez, M. I., Ammari, F., Ivanova, S., & Centeno, M. Á. (2023) · Catalysis Today · doi:10.1016/j.cattod.2023.01.019 · Cited by 11 · see citing works
Microbial conversion of biomass to value-added chemicals
Rabha, J., Devi, S. P., Das, S., Roy, N., & Jha, D. K. (2023) · Elsevier eBooks · doi:10.1016/b978-0-323-89928-4.00018-3 · Cited by 10 · see citing works
Hwang, J. H., Kim, H. J., Kim, S., Lee, Y., Shin, Y., Choi, S., Oh, J., Kim, S., Park, J., Bhatia, S. K., et al. (2024) · Bioresource Technology · doi:10.1016/j.biortech.2024.130355 · Cited by 9 · see citing works
Romashov, L. V., Kucherov, F. A., Kozlov, K. S., & Ananikov, V. P. (2023) · International Journal of Molecular Sciences · doi:10.3390/ijms24043997 · Cited by 8 · see citing works
Santajit, S., Thavorasak, T., Horpet, D., Kong-Ngoen, T., Permpoon, U., Kim, C. Y., Nam, T., & Indrawattana, N. (2025) · Veterinary World · doi:10.14202/vetworld.2025.2181-2193 · Cited by 8 · see citing works
Kim, H.-Y., Park, S.-H., Zuo, G., Kim, K. H., Hwang, S. H., Suh, H., & Lim, S. S. (2021) · Molecules · doi:10.3390/molecules26061639 · Cited by 7 · see citing works
“Because 5-HMF has a possible toxic mechanism [18], we used a Salmonella typhimurium mutagenicity based test (Ames test), which is a suitable bacterial assay to detect mutagenic potential [19].”
MethodKhan, M. T., Hülsemann, B., Krümpel, J., Wüst, D., Oechsner, H., & Lemmer, A. (2022) · Fermentation · doi:10.3390/fermentation8100476 · Cited by 6 · see citing works
“A prime example of such an intermediate is 5-hydroxymethylfurfural (5-HMF), which is perceived as a versatile platform compound due to its broad industrial application spectrum; for instance, in pharmaceuticals, agrochemicals, textiles, plastics, resins, paints, and adhesives to name a few [1,3,4].”
BackgroundАлексеевич, К. Д., Gurov, D. S., Golysheva, A. N., Krasheninnikov, V. G., Erokhin, K. S., & Karlinskii, B. Y. (2025) · Journal of Polymers and the Environment · doi:10.1007/s10924-025-03579-4 · Cited by 5 · see citing works
“It is well known, that the biodegradation effect of gram-positive bacteria on furan compounds is relatively weak [70].”
Kalyaev, M. V., Ryabukhin, D. S., Ivanov, A. Y., Boyarskaya, I. А., Евгеньевна, Б. К., Nikiforova, L. R., Salmova, J. V., Taraskin, A. O., Puzyk, A. M., & Vasilyev, A. V. (2023) · Chemistry of Heterocyclic Compounds · doi:10.1007/s10593-023-03250-7 · Cited by 5 · see citing works
Fong, J. K., Mazo, L., Nairn, A. K., Cordeiro, R. L., Mathieu, Y., Chen, Y., Rovira, C., Walton, P., van Petegem, F., & Brumer, H. (2026) · Biochemical Journal · doi:10.1042/bcj20260010 · Cited by 4 · see citing works
“Interestingly, Fgr AldOx and Cgr AldOx were essentially inactive on aryl aldehydes, including benzaldehyde, cinnamaldehyde, furfural, and 5-hydroxymethylfurfural, the last two of which are of particular interest as biomass-derived platform chemicals [36,51,54,55].”
Sjölin, M., Sayed, M., Espinoza, D., Tallvod, S., & Al‐Rudainy, B. (2025) · Journal of environmental chemical engineering · doi:10.1016/j.jece.2025.115724 · Cited by 4 · see citing works
Sjölin, M., Djärf, M., Ismail, M., Schagerlöf, H., Wallberg, O., Hatti‐Kaul, R., & Sayed, M. (2024) · Catalysts · doi:10.3390/catal14050330 · Cited by 3 · see citing works
Sustainable Downstream Process Design for HMF Conversion to Value-Added Chemicals
Mih�ly, N. B., Prodan, M., Cristea, M. V., & Kiss, A. A. (2025) · Systems and Control Transactions · doi:10.69997/sct.185398 · Cited by 1 · see citing works
Pérez, A. S. L., Mahecha, V. R., Suárez, L. E. C., & Fajardo, C. A. G. (2024) · ChemEngineering · doi:10.3390/chemengineering8060110 · Cited by 1 · see citing works
“Overall, these platform chemicals derived from pea pod waste through hydrothermal processes have significant potential applications across various industries, including energy, agriculture, pharmaceuticals, and materials science, promoting a more sustainable and circular economy [16].”
Ceyhan, K., & Gröger, H. (2025) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.4c08067 · Cited by 1 · see citing works
Shi, Y. (2021) · Queensland University of Technology · doi:10.5204/thesis.eprints.226839
Phan, H. B., Nguyen, K. T., Nguyen, D. L., Nguyen, T. T. H., & Tran, H. P. (2023) · Ministry of Science and Technology Vietnam · doi:10.31276/vjst.65(3).12-17
Engineering enzyme for microenvironment
Rafeeq, H., Hussain, A., Rafique, S., Naqvi, W. Z., & Ramzan, R. (2023) · Elsevier eBooks · doi:10.1016/b978-0-323-91760-5.00007-5
Hwang, J. H., Kim, H. J., Kim, S., Lee, Y., Shin, Y., Choi, S., Oh, J., Kim, S., Park, J., Bhatia, S. K., et al. (2023) · SSRN Electronic Journal · doi:10.2139/ssrn.4652831
Molecular basis of hyper-thermostability in the thermophilic archaeal aldolase MfnB
Maddock, R. M. A., Marsh, C. O., Johns, S. T., Rooms, L. D., Duke, P. W., van der Kamp, M. W., Stach, J. E. M., & Race, P. R. (2024) · Extremophiles · doi:10.1007/s00792-024-01359-x
“This temperature requirement limits the usefulness of M. jannaschii MfnB as a biocatalyst for di-substituted furan production, an important consideration given that such enzymes are highly sought after due to the usefulness of furan heterocycles as fuels and materials (Wang et al. 2018).”
BackgroundCeyhan, K., Rottmann, M., & Gröger, H. (2025) · RSC Sustainability · doi:10.1039/d4su00790e
Nissa, R. C., Irmayanti, M., Nurhamiyah, Y., Fateha, F., Abdullah, A. H. D., Adi, D. T. N., Hidawati, H., Hidayat, H., Ishmayana, S., & Sumiarsa, D. (2025) · Preparative Biochemistry & Biotechnology · doi:10.1080/10826068.2025.2560541
“[25] Therefore, the presence of 5-HMF in the hydrolysates highlights both the challenges and opportunities of designing hydrolysis processes that maximize sugar release while controlling inhibitor formation.”
Microbial conversion of lignocellulosic biomass into valued bioproducts and their chemistry
Dhara, S., Baite, T. N., & Purkait, M. K. (2025) · Elsevier eBooks · doi:10.1016/b978-0-443-21604-6.00003-6
Zhang, X., Zong, Z., & Li, Z. (2025) · Research Square · doi:10.21203/rs.3.rs-7966398/v1
Elouaret, B., Masri, A. N., Hasbullah, H., & Ibrahim, I. M. (2026) · Fuel · doi:10.1016/j.fuel.2026.139296
Small organic molecules through biomass valorization: sustainable routes and applications
Bhatia, S., Bhardwaj, S. R., & Singh, R. (2026) · Frontiers in Environmental Engineering · doi:10.3389/fenve.2026.1867033
Thevarajah, B., Nimarshana, P. H. V., Hanifa, N. M., Dayanath, M., Ariyadasa, T. U., & Chang, J.-S. (2026) · Biochemical Engineering Journal · doi:10.1016/j.bej.2026.110430
- Authors
- Wang, Y., 1 Department of Chemistry and Biochemistry, U. O. N. G.-D., A. Brown, C., Chen, R., & 2 School of Chemical & Biomolecular Engineering, G. I. O. T.
- Affiliations
- University of North Georgia (US)
- Georgia Institute of Technology (US)
- Corresponding author
- Wang, Yu
- Chen, Rachel
- ORCID
- Venue
- AIMS Microbiology
- Published
- 2018
- Volume
- 4
- Issue
- 2
- Pages
- 261-273
- ISSN
- 2471-1888 (ISSN-L)
- PMC
- PMC6604932
- OpenAlex
- W2793721810
- Cited by
- 56
- References
- 64
- Citations by year
- 2026: 4 · 2025: 12 · 2024: 6 · 2023: 10 · 2022: 8 · 2021: 9 · 2020: 5 · 2019: 1 · 2018: 1
- FWCI
- 0.33
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- cc-by
- Locations
- AIMS Microbiology (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Topics
- Physical Sciences › Engineering › Biomedical Engineering › Catalysis for Biomass Conversion
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Microbial Metabolic Engineering and Bioproduction
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Enzyme Catalysis and Immobilization
- Keywords
- 5-hydroxymethylfurfural, furanic compounds, furandicarboxylic acid, biodegradation pathways, microbial production, enzyme mechanism, structure-function relationship, enzyme engineering, biorefinery, bio-based polymers, platform chemicals
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