Abstract
In this work, an effective hybrid strategy was developed for tandem conversion of biomass to furfurylamine with tin-based solid acid Sn-Maifanitum stone and recombinant Escherichia coli whole cells harboring ω-transaminase. 90.3 mM furfural was obtained from corncob (75 g/L) at 170 °C for 0.5 h over Sn-Maifanitum stone catalyst (3.5 wt%) in the aqueous media (pH 1.0), which could be further bioconverted into furfurylamine at 74.0% yield (based on biomass-derived furfural) within 20.5 h. Finally, an efficient recycling and reuse of Sn-Maifanitum stone catalyst and immobilized Escherichia coli AT2018 whole-cell biocatalyst was developed for the synthesis of furfurylamine from biomass in the one-pot reaction system.
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Chen, X., Xue, Y., Hu, J., Tsang, Y. F., & Gao, M.-T. (2017). Release of polyphenols is the major factor influencing the bioconversion of rice straw to lactic acid. Applied Biochemistry and Biotechnology, 183, 685–698.
Li, G., Li, N., Zheng, M., Li, S. S., Wang, A., Cong, Y., Wang, X., & Zhang, T. (2016). Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose. Green Chemistry, 18, 3607–3613.
Li, J., Ding, D., Xu, L. J., Guo, Q. X., & Fu, Y. (2014). The breakdown of reticent biomass to soluble components and their conversion to levulinic acid as a fuel precursor. RSC Advances, 4, 14985–14992.
Xu, J., Sheng, Z., Wang, X., Liu, X., Xia, J., Xiong, P., & He, B. (2016). Enhancement in ionic liquid tolerance of cellulase immobilized on PEGylated graphene oxide nanosheets: application in saccharification of lignocellulose. Bioresource Technology, 200, 1060–1064.
Nishimura, S., Mizuhori, K., & Ebitani, K. (2015). Reductive amination of furfural toward furfurylamine with aqueous ammonia under hydrogen over Ru-supported catalyst. Research on Chemical Intermediates, 42, 19–30.
Karinen, R., & Niemelä, K. V. M. (2011). Biorefining: heterogeneously catalyzed reactions of carbohydrates for the production of furfural and hydroxymethylfurfural. ChemSusChem, 4, 1002–1016.
Steinbach, D., Kruse, A., & Sauer, J. (2017). Pretreatment technologies of lignocellulosic biomass in water in view of furfural and 5-hydroxymethylfurfural production- a review. Biomass Conversion and Biorefinery, 7, 247–274.
Tong, X., Zhang, Z., Gao, Y., Zhang, Y., Yu, L., & Li, Y. (2019). Selective carbon-chain increasing of renewable furfural utilizing oxidative condensation reaction catalyzed by mono-dispersed palladium oxide. Molecular Catalysis, 477. https://doi.org/10.1016/j.mcat.2019.110545.
Millán, G. G., Phir, J., Mäkelä, M., Maloney, T., Balu, A. M., Pineda, A., Llorca, J., & Sixta, H. (2019). Furfural production in a biphasic system using a carbonaceous solid acid catalyst. Applied Catalysis A: General, 585, 117180.
Wang, K. F., Liu, C. L., Sui, K. Y., Guo, C., & Liu, C. Z. (2018). Efficient catalytic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid by magnetic laccase catalyst. ChemBioChem, 19, 654–659.
Nguyen-Huy, C., Kim, J. S., Yoon, S., Yang, E., Kwak, J. H., Lee, M. S., & An, K. (2018). Supported Pd nanoparticle catalysts with high activities and selectivities in liquid-phase furfural hydrogenation. Fuel, 226, 607–617.
Ma, Y. F., Wang, H., Xu, G. Y., Liu, X. H., Zhang, Y., & Fu, Y. (2017). Selective conversion of furfural to cyclopentanol over cobalt catalysts in one step. Chinese Chemical Letters, 28, 1153–1158.
Gupta, N. K., Fukuoka, A., & Nakajima, K. (2017). Amorphous Nb2O5 as a selective and reusable catalyst for furfural production from xylose in biphasic water and toluene. ACS Catalysis, 7, 2430–2436.
Liu, L., Lou, H., & Chen, M. (2016). Selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over Ni/CNTs and bimetallic Cu Ni/CNTs catalysts. International Journal of Hydrogen Energy, 41, 14721–14731.
Liu, H., Huang, Z., Zhao, F., Cui, F., Li, X., Xia, C., & Chen, J. (2016). Efficient hydrogenolysis of biomass-derived furfuryl alcohol to 1,2- and 1,5-pentanediols over nonprecious Cu-Mg3AlO4.5 bifunctional catalyst. Catalysis Science & Technology, 6, 668–671.
Liu, Y., Zhou, K., Shu, H., Liu, H., Lou, J., Guo, D., Wei, Z., & Li, X. (2017). Switchable synthesis of furfurylamine and tetrahydrofurfurylamine from furfuryl alcohol over RANEY® nickel. Catalysis Science & Technology, 7, 4129–4135.
Zhang, L., Tian, L., Sun, R., Liu, C., Kou, H., & Zuo, H. (2019). Transformation of corncob into furfural by a bifunctional solid acid catalyst. Bioresource Technology, 276, 60–64.
Xue, X. X., Di, J. H., He, Y. C., Wang, B. Q., & Ma, C. L. (2018). Effective utilization of carbohydrate in corncob to synthesize furfuralcohol by chemical–enzymatic catalysis in toluene–water media. Applied Biochemistry and Biotechnology, 185, 42–54.
Chen, F. F., Zheng, G. W., Liu, L., Li, H., Chen, Q., Li, F., Li, C., & Xu, J. H. (2018). Reshaping the active pocket of amine dehydrogenases for asymmetric synthesis of bulky aliphatic amines. ACS Catalysis, 8, 2622–2628.
Zhang, J. D., Zhao, J., Gao, L., Chang, H., Wei, W., & Xu, J. (2019). Enantioselective synthesis of enantiopure beta-amino alcohols via kinetic resolution and asymmetric reductive amination by a robust transaminase from Mycobacterium vanbaalenii. Journal of Biotechnology, 290, 24–32.
Mullangi, D., Chakraborty, D., Pradeep, A., Koshti, V., Vinod, C. P., Panja, S., Nair, S., & Vaidhyanathan, R. (2018). Highly stable COF-supported Co/Co(OH)2 nanoparticles heterogeneous catalyst for reduction of nitrile/nitro compounds under mild conditions. Small, 14, e1801233.
Liu, Z. Q., Wu, L., Zheng, L., Wang, W. Z., Zhang, X. J., Jin, L. Q., & Zheng, Y. G. (2018). Biosynthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate by carbonyl reductase from Rhodosporidium toruloides in mono and biphasic media. Bioresource Technology, 249, 161–167.
Zhang, Z. J., Cai, R. F., & Xu, J. H. (2018). Characterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-beta-amino acids. Applied Microbiology and Biotechnology, 201, 6047–6056.
Gomm, A., & O'Reilly, E. (2018). Transaminases for chiral amine synthesis. Current Opinion in Chemical Biology, 43, 106–112.
Zhang, P., Liao, X., Ma, C., Li, Q., Li, A., & He, Y. (2019). Chemoenzymatic conversion of corncob to furfurylamine via tandem catalysis with tin-based solid acid and transaminase biocatalyst. ACS Sustainable Chemistry & Engineering, 7(21), 17636–17642.
Höhne, M., Schätzle, S., Jochens, H., Robins, K., & Bornscheuer, U. T. (2010). Rational assignment of key motifs for function guides in silico enzyme identification. Nature Chemical Biology, 6, 807–813.
He, Y., Xu, J., Su, J., & Zhou, L. (2010). Bioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401. Applied Biochemistry and Biotechnology, 160, 1428–1440.
Mallin, H., Hohne, M., & Bornscheuer, U. T. (2014). Immobilization of (R)- and (S)-amine transaminases on chitosan support and their application for amine synthesis using isopropylamine as donor. Journal of Biotechnology, 191, 32–37.
Shin, G., Mathew, S., & Yun, H. (2015). Kinetic resolution of amines by (R)-selective omega-transaminase from Mycobacterium vanbaalenii. Journal of Industrial and Engineering Chemistry, 23, 128–133.
Zhang, J. D., Yang, X. X., Jia, Q., Zhao, J. W., Gao, L. L., Gao, W. C., Chang, H. H., Wei, W. L., & Xu, J. H. (2019). Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system. Catalysis Science & Technology, 9, 70–74.
Hassan, S. S., Williams, G. A., & Jaiswal, A. K. (2018). Emerging technologies for the pretreatment of lignocellulosic biomass. Bioresource Technology, 262, 310–318.
Norimasa Kashiwagi, N., Ogino, C., & Kondo, A. (2017). Production of chemicals and proteins using biomass-derived substrates from a Streptomyces host. Bioresource Technology, 245, 1655–1663.
Sawatdeenarunat, C., Nam, H., Adhikari, S., Sung, S., & Kumar Khanal, S. (2018). Decentralized biorefinery for lignocellulosic biomass: integrating anaerobic digestion with thermochemical conversion. Bioresource Technology, 250, 140–147.
Audemar, M., Ciotonea, C., De Oliveira Vigier, K., Royer, S., Ungureanu, A., Dragoi, B., Dumitriu, E., & Jérôme, F. (2015). Selective hydrogenation of furfural to furfuryl alcohol in the presence of a recyclable cobalt/SBA-15 catalyst. ChemSusChem, 8, 1885–1891.
Casoni, A. I., Hoch, P. M., Volpe, M. A., & Gutierrez, V. S. (2018). Catalytic conversion of furfural from pyrolysis of sunflower seed hulls for producing bio-based furfuryl alcohol. Journal of Cleaner Production, 178, 237–246.
Sweygers, N., Harrer, J., Dewil, R., & Appels, L. (2018). A microwave-assisted process for the in-situ production of 5-hydroxymethylfurfural and furfural from lignocellulosic polysaccharides in a biphasic reaction system. Journal of Cleaner Production, 187, 1014–1024.
Wang, A., Balsara, N. P., & Bell, A. T. (2016). Pervaporation-assisted catalytic conversion of xylose to furfural. Green Chemistry, 18, 4073–4085.
Jing, X., Zhang, X., & Bao, J. (2009). Inhibition performance of lignocellulose degradation products on industrial cellulase enzymes during cellulose hydrolysis. Applied Biochemistry and Biotechnology, 159, 696–707.
Yang, Y. L., Ma, J. P., Jia, X. Q., Du, Z. T., Duan, Y., & Xu, J. (2016). Aqueous phase hydrogenation of furfural to tetrahydrofurfuryl alcohol on alkaline earth metal modified Ni/Al2O3. RSC Advances, 6, 51221–51228.
Jimenez-Gomez, C. P., Cecilia, J. A., Duran-Martin, D., Moreno-Tost, R., Santamaria-Gonzalez, J., Merida-Robles, J., Mariscal, R., & Maireles-Torres, P. (2016). Gas-phase hydrogenation of furfural to furfuryl alcohol over Cu/ZnO catalysts. Journal of Catalysis, 336, 107–115.
Shen, G., Zhang, S., Lei, Y., Chen, Z., & Yin, G. (2018). Synthesis of 2,5-furandicarboxylic acid by catalytic carbonylation of renewable furfural derived 5-bromofuroic acid. Molecular Catalysis, 455, 204–209.
Michèle, B., Pierre, G., & Catherine, P. (2013). Conversion of biomass into chemicals over metal catalysts. Chem. Res., 114, 1827–1870.
Xia, Z. H., Zong, M. H., & Li, N. (2020). Catalytic synthesis of 2,5-bis(hydroxymethyl)furan from 5-hydroxymethylfurfual by recombinant Saccharomyces cerevisiae. Enzyme and Microbial Technology, 134, 109491.
Richter, N., Farnberger, J. E., Pressnitz, D., Lechner, H., Zepeck, F., & Kroutil, W. (2015). A system for ω-transaminase mediated (R)-amination using l-alanine as an amine donor. Green Chemistry, 17, 2952–2958.
Funding
This work was supported by a grant from the National Key Research and Development Program of China (No. 2019YFA09005000), the National Natural Science Foundation of China (No. 21978072), the Hubei Provincial Natural Science Foundation of China (2018CFA019), the Science and Technology Innovation Program of Hubei Province (2018ABA098, 2018ABA096), the Central Committee Guides Local Science and Technology Development Projects (2018ZYYD034), the Open Project of State Key Laboratory of Biocatalysis and Enzyme Engineering (China) (No. SKLBEE2018008), and the Open Project of Jiangsu Key Laboratory for Biomassbased Energy and Enzyme Technology (No. BEETKB1902).
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Liao, XL., Li, Q., Yang, D. et al. An Effective Hybrid Strategy for Conversion of Biomass into Furfurylamine by Tandem Pretreatment and Biotransamination. Appl Biochem Biotechnol 192, 794–811 (2020). https://doi.org/10.1007/s12010-020-03334-6
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DOI: https://doi.org/10.1007/s12010-020-03334-6