5-羟甲基糠醛的生物催化氧化研究进展

doi:10.13560/j.cnki.biotech.bull.1985.2016.09.008

生物技术通报 ›› 2016, Vol. 32 ›› Issue (9): 50-58.doi: 10.13560/j.cnki.biotech.bull.1985.2016.09.008

5-羟甲基糠醛的生物催化氧化研究进展

吴树丽^{1, 2}, 刘启顺², 谭海东², 张付云¹, 尹恒²

1. 大连海洋大学食品科学与工程学院,大连 116000; 2. 中国科学院大连化学物理研究所天然产物与糖工程组,大连 116000

收稿日期:2016-02-24 出版日期:2016-09-25 发布日期:2016-10-10
作者简介:吴树丽,女,硕士研究生,研究方向：生物催化氧化5-羟甲基糠醛;E-mail：wushuli219@163.com
基金资助:
中科院青年创新促进会（2015144）,“863”项目（2012AA021205-2）,中科院STS项目（KFJ-EW-STS077-）

Research Progress on Biocatalytic Oxidation of 5-hydroxymethylfurfural

WU Shu-li, LIU Qi-shun, TAN Hai-dong, ZHANG Fu-yun, YIN Heng

1. College of Food Science and Engineering,Dalian Ocean University,Dalian 116000; 2. Natural Products and Glyco-Biotechnology,Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian 116023

Received:2016-02-24 Published:2016-09-25 Online:2016-10-10

摘要/Abstract

摘要： 5-羟甲基糠醛HMF是重要的生物基平台化合物,将HMF氧化成呋喃类化合物是生物质转化的重要发展方向。生物催化具有选择性高、反应条件温和,环境友好等优势。近年来生物催化氧化HMF广受关注。从HMF生物转化过程的发现、HMF在微生物的代谢过程以及全细胞转化和酶法催化HMF氧化3个方面对该领域的研究进行综述,并对HMF的生物催化氧化过程发展方向进行展望,以期为绿色高效催化5-羟甲基糠醛制备呋喃类大宗化学品奠定理论基础。

关键词: 5-羟甲基糠醛, 生物催化氧化, 呋喃类大宗化学品

Abstract: 5-hydroxymethylfurfural（HMF）is an important bio-based platform chemical. Oxidation of HMF to furan chemicals is a crucial developing orientation of biomass conversion. In recent years,with the advantages of high selectivity,mild reaction conditions,and environment friendly,the biocatalytic oxidation of HMF has attracted extensive attentions. In this paper,we reviewed the discovery of biotransformation process,microbial metabolism,whole-cell biotransformation and the enzymatic catalytic oxidation of HMF. Finally,we provided the development prospect of bio-catalytic oxidation of HMF in the future,aiming at providing the theoretical foundation for the green and efficient conversion of HMF to furan bulk chemicals.

Key words: 5-hydroxymethylfurfural, biocatalytic oxidation, furan bulk chemicals

吴树丽, 刘启顺, 谭海东, 张付云, 尹恒. 5-羟甲基糠醛的生物催化氧化研究进展[J]. 生物技术通报, 2016, 32(9): 50-58.

WU Shu-li^{1, 2}, LIU Qi-shun², TAN Hai-dong², ZHANG Fu-yun¹, YIN Heng². Research Progress on Biocatalytic Oxidation of 5-hydroxymethylfurfural[J]. Biotechnology Bulletin, 2016, 32(9): 50-58.

参考文献

[1] Rosatella AA, Simeonov SP, Frade RFM, et al. 5-Hydroxymethylfur-fural（HMF）as a building block platform：Biological properties, synthesis and synthetic applications[J]. Green Chemistry, 2011, 13：754-793.
[2] Lilga MA, Hallen RT, Gray M. Production of Oxidized Derivatives of 5-Hydroxymethylfurfural（HMF）[J]. Topics in Catalysis, 2010, 53：1264-1269.
[3] Du Z, Ma J, Wang F, et al. Oxidation of 5-hydroxymethylfurfural to maleic anhydride with molecular oxygen[J]. Green Chemistry, 2011, 13：554-557.
[4] Gandini A, Silvestre AJD, Neto CP, et al. The furan counterpart of poly（ethylene terephthalate）：An alternative material based on renewable resources[J]. Journal of Polymer Science Part A：Polymer Chemistry, 2009, 47：295-298.
[5] Werpy T, Petersen G. Top value added chemicals from biomass：volume I—results of Screening for potential candidates from sugars and synthesis gas[R]. US：Produced by the Staff at Pacific Northwest National Laboratory（PNNL）National Renewable Energy Laboratory（NREL）Office of Biomass Program（EERE）For the Office of the Biomass Program, 2004.
[6] Jong Ed, Higson A, Walsh P, et al. Bio-based Chemicals Value Added Products from Biorefinerie[R]. 2012.
[7] Hopkins KT, Wilson WD, Bender BC, et al. Extended aromatic furan amidino derivatives as anti-pneumocystis carinii agents[J]. Medicinal Chemistry, 1998, 41：3872-3878.
[8] Ma J, Du Z, Xu J, et al. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran, and synthesis of a fluorescent material[J]. Chemistry and Sustainable Chemistry, 2011, 4：51-54.
[9] Hirai H. Oligomers from hydroxymethylfurancarboxylic acid[J]. Journal of Macromolecular Science：Part A - Chemistry, 2006, 21：1165-1179.
[10] Braisted AC, Oslob JD, Delano WL, et al. Discovery of a potent small molecule IL-2 inhibitor through fragment assembly[J]. Journal of American Chemical Society, 2013, 125：3714-3715.
[11] Nie J, Xie J, Liu H. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran on supported Ru catalysts[J]. Journal of Catalysis, 2013, 301：83-91.
[12] Amarasekara AS, Green D, McMillan E. Efficient oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran using Mn（III）-salen catalysts[J]. Catalysis Communications, 2008, 9：286-288.
[13] Halliday GA, Young RJ Jr, Grushin VV. One-pot, two-step, practical catalytic synthesis of 2, 5-diformylfuran from fructose[J]. Organic Letters, 2003, 5（11）：2003-2005.
[14] Siankevich S, Savoglidis G, Fei Z, et al. A novel platinum nanocatalyst for the oxidation of 5-Hydroxymethylfurfural into 2, 5-furandicarboxylic acid under mild conditions[J]. Journal of Catalysis, 2014, 315：67-74.
[15] Gorbanev YY, Klitgaard SK, Woodley JM, et al. Gold-catalyzed aerobic oxidation of 5-hydroxymethylfurfural in water at ambient temperature[J]. Chemistry and Sustainable Chemistry, 2009, 2：672-675.
[16] Zhang Z, Zhen J, Liu B, et al. Selective aerobic oxidation of the biomass-derived precursor 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid under mild conditions over a magnetic palladium nanocatalyst[J]. Green Chemistry, 2015, 17：1308-1317.
[17] Liu ZL, Slininger PJ, Dien BS, et al. Adaptive response of yeasts to furfural and 5-hydroxymethylfurfural and new chemical evidence for HMF conversion to 2, 5-bis-hydroxymethylfuran[J]. Journal of Industrial Microbiology and Biotechnology, 2004, 31：345-352.
[18] Palmqvist E, Hahn-Hägerdal B. Fermentation of lignocellulosic hydrolysates. I：inhibition and detoxification[J]. Bioresource Technology, 1999（2000）：74：17-24.
[19] Lopez MJ, Nichols NN, Dien BS, et al. Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates[J]. Applied Microbiology and Biotechnology, 2004, 64：125-131.
[20] Zhang J, Zhu Z, Wang X, et al. Biodetoxification of toxins generated from lignocellulose pretreatment using a newly isolated fungus, Amorphotheca resinae ZN1, and the consequent ethanol fermentation[J]. Biotechnolology for Biofuels, 2010, 3：26.
[21] Wierckx N, Koopman F, Bandounas L, et al. Isolation and characterization of Cupriavidus basilensis HMF14 for biological removal of inhibitors from lignocellulosic hydrolysate[J]. Microbial Biotechnology, 2010, 3：336-343.
[22] Koopman F, Wierckx N, de Winde JH, et al. Identification and characterization of the furfural and 5-（hydroxymethyl）furfural degradation pathways of Cupriavidus basilensis HMF14[J]. Proceedings of the National Academy of Sciences of the United States of America, 2010, 107：4919-4924.
[23] Feldman D, Kowbel DJ, Glass NL, et al. Detoxification of 5-hydroxymethylfurfural by the Pleurotus ostreatus lignolytic enzymes aryl alcohol oxidase and dehydrogenase[J]. Biotechnology for Biofuels, 2015, 8：63.
[24] Jimenez DJ, Korenblum E, van Elsas JD. Novel multispecies microbial consortia involved in lignocellulose and 5-hydroxymethylfurfural bioconversion[J]. Applied Microbiology and Biotechnology, 2014, 98：2789-2803.
[25] Trudgill PW. The metabolism of 2-furoic acid by pseudomonas F2[J]. Biochemistry. , 1969, 113：577-587.
[26] Ran H, Zhang J, Gao Q, et al. Analysis of biodegradation performance of furfural and 5-hydroxymethylfurfural by Amorphotheca resinae ZN1[J]. Biotechnology for Biofuels, 2014, 7：51.
[27] Wierckx N, Koopman F, Ruijssenaars HJ, et al. Microbial degradation of furanic compounds：biochemistry, genetics, and impact[J]. Applied Microbiology and Biotechnology, 2011, 92：1095-1105.
[28] Koopman F, Wierckx N, de Winde JH, et al. Efficient whole-cell biotransformation of 5-（hydroxymethyl）furfural into FDCA, 2, 5-furandicarboxylic acid[J]. Bioresour Technology, 2010, 101：6291-6296.
[29] Krystof M, Perez-Sanchez M, Dominguez de Maria P. Lipase-media-ted selective oxidation of furfural and 5-hydroxymethylfurfural[J]. Chemistry and Sustainable Chemistry, 2013, 6：826-830.
[30] Dijkman WP, Fraaije MW. Discovery and Characterization of a 5-hydroxymethylfurfural oxidase from methylovorussp. strain MP688[J]. Applied and Environmental Microbiology, 2014, 80：1082-1090.
[31] Dijkman WP, Groothuis DE, Fraaije MW. Enzyme-catalyzed oxidation of 5-hydroxymethylfurfural to furan-2, 5-dicarboxylic acid[J]. Angewandte Chemie International Edition, 2014, 53：6515-6518.
[32] Dijkman WP, Binda C, Fraaije MW, et al. Structure-based enzyme tailoring of 5-hydroxymethylfurfural oxidase[J]. ACS Catalysis, 2015, 5：1833-1839.
[33] Carro J, Ferreira P, Rodriguez L, et al. 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase[J]. FEBS Journal, 2015, 282（16）：3218-3229.
[34] Qin YZ, Li YM, Zong MH, et al. Enzyme-catalyzed selective oxidation of 5-hydroxymethylfurfural（HMF）and separation of HMF and 2, 5-diformylfuran using deep eutectic solvents[J]. Green Chemistry, 2015, 17：3718-3722.
[35] McKenna SM, Leimkühler S, Herter S, et al. Enzyme cascade reactions：synthesis of furandicarboxylic acid（FDCA）and carboxylic acids using oxidases in tandem[J]. Green Chemistry. , 2015, 17：3271-3275.
[36] van Deurzen MPJ, van Rantwijk F, Sheldon RA. Chloroperoxidase-Catalyzed Oxidation of 5-Hydroxymethylfurfural[J]. Journal of Carbohydrate Chemistry, 1997, 16：299-309.

5-羟甲基糠醛的生物催化氧化研究进展

Research Progress on Biocatalytic Oxidation of 5-hydroxymethylfurfural

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