Novel Nano-/Micro-Biocatalyst: Soybean Epoxide Hydrolase Immobilized on UiO-66-NH2 MOF for Efficient Biosynthesis of Enantiopure (R)-1, 2-Octanediol in Deep Eutectic Solvents

ACS Sustainable Chemistry and Engineering

Volumn 4, Issue 6, 2016, Pages 3586-3595

  Cao, Shi Lin ^a,b   Yue, Dong Mei ^a   Li, Xue Hui ^a   Smith, Thomas J ^c   Li, Ning ^a   Zong, Min Hua ^a   Wu, Hong ^a   Ma, Yong Zheng ^b   Lou, Wen Yong ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^c SHEFFIELD HALLAM UNIVERSITY   (United Kingdom)

Author keywords

Deep eutectic solvent; Dipeptide; Epoxide hydrolase; Green chemistry; Metal organic framework; Optically active vicinal diols; Sustainable chemistry

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CRYSTALLINE MATERIALS; ENZYME IMMOBILIZATION; ENZYMES; EUTECTICS; HYDROLASES; IONIC LIQUIDS; JAVA PROGRAMMING LANGUAGE; ORGANOMETALLICS; PH EFFECTS; SOLVENTS;

DEEP EUTECTIC SOLVENTS; DI-PEPTIDES; EPOXIDE HYDROLASES; GREEN CHEMISTRY; METAL ORGANIC FRAMEWORK; SUSTAINABLE CHEMISTRY; VICINAL DIOLS;

ENZYME ACTIVITY;

EID: 84973441096     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.6b00777     Document Type: Article

References (58)

1. Zhou, H.-C.; Long, J. R.; Yaghi, O. M. Introduction to Metal-Organic Frameworks Chem. Rev. 2012, 112, 673-674 10.1021/cr300014x
2. Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Reticular Synthesis and the Design of New Materials Nature 2003, 423, 705-714 10.1038/nature01650
3. Imaz, I.; Rubio-Martínez, M.; An, J.; Sole-Font, I.; Rosi, N. L.; Maspoch, D. Metal-Biomolecule Frameworks (Mbiofs) Chem. Commun. 2011, 47, 7287-7302 10.1039/c1cc11202c
4. Stock, N.; Biswas, S. Synthesis of Metal-Organic Frameworks (Mofs): Routes to Various Mof Topologies, Morphologies, and Composites Chem. Rev. 2012, 112, 933-969 10.1021/cr200304e
5. Czaja, A. U.; Trukhan, N.; Müller, U. Industrial Applications of Metal-Organic Frameworks Chem. Soc. Rev. 2009, 38, 1284-1293 10.1039/b804680h
6. Greathouse, J. A.; Kinnibrugh, T. L.; Allendorf, M. D. Adsorption and Separation of Noble Gases by Irmof-1: Grand Canonical Monte Carlo Simulations Ind. Eng. Chem. Res. 2009, 48, 3425-3431 10.1021/ie801294n
7. Kanoo, P.; Gurunatha, K. L.; Maji, T. K. Versatile Functionalities in Mofs Assembled from the Same Building Units: Interplay of Structural Flexibility, Rigidity and Regularity J. Mater. Chem. 2010, 20, 1322-1331 10.1039/B917029D
8. Savonnet, M.; Aguado, S.; Ravon, U.; Bazer-Bachi, D.; Lecocq, V.; Bats, N.; Pinel, C.; Farrusseng, D. Solvent Free Base Catalysis and Transesterification over Basic Functionalised Metal-Organic Frameworks Green Chem. 2009, 11, 1729-1732 10.1039/b915291c
9. Sun, C.-Y.; Liu, S.-X.; Liang, D.-D.; Shao, K.-Z.; Ren, Y.-H.; Su, Z.-M. Highly Stable Crystalline Catalysts Based on a Microporous Metal- Organic Framework and Polyoxometalates J. Am. Chem. Soc. 2009, 131, 1883-1888 10.1021/ja807357r
10. Chen, J.; Li, K.; Chen, L.; Liu, R.; Huang, X.; Ye, D. Conversion of Fructose into 5-Hydroxymethylfurfural Catalyzed by Recyclable Sulfonic Acid-Functionalized Metal-Organic Frameworks Green Chem. 2014, 16, 2490-2499 10.1039/c3gc42414f
11. Lykourinou, V.; Chen, Y.; Wang, X.-S.; Meng, L.; Hoang, T.; Ming, L.-J.; Musselman, R. L.; Ma, S. Immobilization of Mp-11 into a Mesoporous Metal-Organic Framework, Mp-11@ Mesomof: A New Platform for Enzymatic Catalysis J. Am. Chem. Soc. 2011, 133, 10382-10385 10.1021/ja2038003
12. Xie, B.; Jia, H.; Xie, Y.; Wei, P. Immobilized Laccase and Its Properties by Metal Organic Framework Mof-199 Chin. J. Bioproc. Eng. 2011, 5, 003
13. Liu, W. L.; Yang, N. S.; Chen, Y. T.; Lirio, S.; Wu, C. Y.; Lin, C. H.; Huang, H. Y. Lipase-Supported Metal-Organic Framework Bioreactor Catalyzes Warfarin Synthesis Chem.-Eur. J. 2015, 21, 115-119 10.1002/chem.201405252
14. Larsen, R. W.; Wojtas, L.; Perman, J.; Musselman, R. L.; Zaworotko, M. J.; Vetromile, C. M. Mimicking Heme Enzymes in the Solid State: Metal-Organic Materials with Selectively Encapsulated Heme J. Am. Chem. Soc. 2011, 133, 10356-10359 10.1021/ja203068u
15. Chen, Y.; Lykourinou, V.; Hoang, T.; Ming, L.-J.; Ma, S. Size-Selective Biocatalysis of Myoglobin Immobilized into a Mesoporous Metal-Organic Framework with Hierarchical Pore Sizes Inorg. Chem. 2012, 51, 9156-9158 10.1021/ic301280n
16. Liu, W.-L.; Lo, S.-H.; Singco, B.; Yang, C.-C.; Huang, H.-Y.; Lin, C.-H. Novel Trypsin-Fitc@ Mof Bioreactor Efficiently Catalyzes Protein Digestion J. Mater. Chem. B 2013, 1, 928-932 10.1039/c3tb00257h
17. Chen, Y.; Lykourinou, V.; Vetromile, C.; Hoang, T.; Ming, L.-J.; Larsen, R. W.; Ma, S. How Can Proteins Enter the Interior of a Mof? Investigation of Cytochrome C Translocation into a Mof Consisting of Mesoporous Cages with Microporous Windows J. Am. Chem. Soc. 2012, 134, 13188-13191 10.1021/ja305144x
18. Huo, J.; Aguilera-Sigalat, J.; El-Hankari, S.; Bradshaw, D. Magnetic Mof Microreactors for Recyclable Size-Selective Biocatalysis Chem. Sci. 2015, 6, 1938 10.1039/C4SC03367A
19. Shih, Y. H.; Lo, S. H.; Yang, N. S.; Singco, B.; Cheng, Y. J.; Wu, C. Y.; Chang, I.; Huang, H. Y.; Lin, C. H. Trypsin-Immobilized Metal-Organic Framework as a Biocatalyst in Proteomics Analysis ChemPlusChem 2012, 77, 982-986 10.1002/cplu.201200186
20. Luan, Y.; Qi, Y.; Gao, H.; Zheng, N.; Wang, G. Synthesis of an Amino-Functionalized Metal-Organic Framework at a Nanoscale Level for Gold Nanoparticle Deposition and Catalysis J. Mater. Chem. A 2014, 2, 20588-20596 10.1039/C4TA04311A
21. Cao, S.-L.; Li, X.-H.; Lou, W.-Y.; Zong, M.-H. Preparation of a Novel Magnetic Cellulose Nanocrystal and Its Efficient Use for Enzyme Immobilization J. Mater. Chem. B 2014, 2, 5522-5530 10.1039/C4TB00584H
22. Cao, S.-L.; Xu, H.; Li, X.-H.; Lou, W.-Y.; Zong, M.-H. Papain@Magnetic Nanocrystalline Cellulose Nanobiocatalyst: A Highly Efficient Biocatalyst for Dipeptide Biosynthesis in Deep Eutectic Solvents ACS Sustainable Chem. Eng. 2015, 3, 1589-1599 10.1021/acssuschemeng.5b00290
23. Cao, S.-L.; Huang, Y.-M.; Li, X.-H.; Xu, P.; Wu, H.; Li, N.; Lou, W.-Y.; Zong, M.-H. Preparation and Characterization of Immobilized Lipase from Pseudomonas Cepacia onto Magnetic Cellulose Nanocrystals. Sci. Rep. 2016, 6, 20420 10.1038/srep20420
24. Mateo, L.F.S.a.C. Improvement of the Epoxidehydrolase Properties for the Enantioselective Hydrolysis of Epoxides Curr. Org. Chem. 2013, 17, 744-755 10.2174/1385272811317070008
25. Crosby, J. Chirality in Industry-an Overview Chiral. Ind. 1992, 1-66
26. Chen, Y.; Chen, C.; Wu, X. Dicarbonyl Reduction by Single Enzyme for the Preparation of Chiral Diols Chem. Soc. Rev. 2012, 41, 1742-1753 10.1039/c1cs15230k
27. Kumar, R.; Wani, S. I.; Chauhan, N. S.; Sharma, R.; Sareen, D. Cloning and Characterization of an Epoxide Hydrolase from Cupriavidus Metallidurans-Ch34 Protein Expression Purif. 2011, 79, 49-59 10.1016/j.pep.2011.04.007
28. Martins, M. P.; Mouad, A. M.; Boschini, L.; Seleghim, M. H. R.; Sette, L. D.; Porto, A. L. M. Marine Fungi Aspergillus Sydowii and Trichoderma Sp. Catalyze the Hydrolysis of Benzyl Glycidyl Ether Mar. Biotechnol. 2011, 13, 314-320 10.1007/s10126-010-9302-2
29. Woo, J.-H.; Lee, E. Y. Enantioselective Hydrolysis of Racemic Styrene Oxide and Its Substituted Derivatives Using Newly-Isolated Sphingopyxis Sp. Exhibiting a Novel Epoxide Hydrolase Activity Biotechnol. Lett. 2014, 36, 357-362 10.1007/s10529-013-1373-5
30. Lee, E. Y.; Shuler, M. L. Molecular Engineering of Epoxide Hydrolase and Its Application to Asymmetric and Enantioconvergent Hydrolysis Biotechnol. Bioeng. 2007, 98, 318-327 10.1002/bit.21444
31. Chen, W. J.; Lou, W. Y.; Wang, X. T.; Zong, M. H.. Asymmetric Hydrolysis of Styrene Oxide Catalyzed by Mung Bean Epoxide Hydrolase in Organic Solvent/Buffer Biphasic System. Cuihua Xuebao 2011, 32, 1557 10.3724/SP.J.1088.2011.10606
32. Botes, A. L.; Weijers, C.; van Dyk, M. S. Biocatalytic Resolution of 1,2-Epoxyoctane Using Resting Cells of Different Yeast Strains with Novel Epoxide Hydrolase Activities Biotechnol. Lett. 1998, 20, 421-426 10.1023/A:1005395817739
33. Krieg, H. M.; Botes, A. L.; Smith, M. S.; Breytenbach, J. C.; Keizer, K. The Enantioselective Catalytic Hydrolysis of Racemic 1,2-Epoxyoctane in a Batch and a Continuous Process J. Mol. Catal. B: Enzym. 2001, 13, 37-47 10.1016/S1381-1177(00)00229-0
34. Krieg, H. M.; Breytenbach, J. C.; Keizer, K. Resolution of 1,2-Epoxyoctane by Enantioselective Catalytic Hydrolysis in a Membrane Bioreactor J. Membr. Sci. 2000, 180, 69-80 10.1016/S0376-7388(00)00525-1
35. Chen, W. J.; Lou, W. Y.; Zong, M. H. Efficient Asymmetric Hydrolysis of Styrene Oxide Catalyzed by Mung Bean Epoxide Hydrolases in Ionic Liquid-Based Biphasic Systems Bioresour. Technol. 2012, 115, 58-62 10.1016/j.biortech.2011.10.072
36. Yu, C.-Y.; Li, X.-F.; Lou, W.-Y.; Zong, M.-H. Cross-Linked Enzyme Aggregates of Mung Bean Epoxide Hydrolases: A Highly Active, Stable and Recyclable Biocatalyst for Asymmetric Hydrolysis of Epoxides J. Biotechnol. 2013, 166, 12 10.1016/j.jbiotec.2013.04.015
37. JU Xin, P. J.; Jianhe, X. U. Enantioconvergent Hydrolysis of P-Nitrostyrene Oxide Catalyzed by Mung Bean Epoxide Hydrolase Chin. J. Catal. 2008, 29, 696-700
38. Yu, C.-Y.; Wei, P.; Li, X.-F.; Zong, M.-H.; Lou, W.-Y. Using Ionic Liquid in a Biphasic System to Improve Asymmetric Hydrolysis of Styrene Oxide Catalyzed by Cross-Linked Enzyme Aggregates (Cleas) of Mung Bean Epoxide Hydrolases Ind. Eng. Chem. Res. 2014, 53, 7923-7930 10.1021/ie4037559
39. Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. K.; Tambyrajah, V. Novel Solvent Properties of Choline Chloride/Urea Mixtures Chem. Commun. 2003, 70-71 10.1039/b210714g
40. Durand, E.; Lecomte, J.; Baréa, B.; Piombo, G.; Dubreucq, E.; Villeneuve, P. Evaluation of Deep Eutectic Solvents as New Media for Candida Antarctica B Lipase Catalyzed Reactions Process Biochem. 2012, 47, 2081-2089 10.1016/j.procbio.2012.07.027
41. Lindberg, D.; de la Fuente Revenga, M.; Widersten, M. Deep Eutectic Solvents (Dess) Are Viable Cosolvents for Enzyme-Catalyzed Epoxide Hydrolysis J. Biotechnol. 2010, 147, 169-171 10.1016/j.jbiotec.2010.04.011
42. Kandiah, M.; Nilsen, M. H.; Usseglio, S.; Jakobsen, S.; Olsbye, U.; Tilset, M.; Larabi, C.; Quadrelli, E. A.; Bonino, F.; Lillerud, K. P. Synthesis and Stability of Tagged Uio-66 Zr-Mofs Chem. Mater. 2010, 22, 6632-6640 10.1021/cm102601v
43. Cavka, J. H.; Jakobsen, S.; Olsbye, U.; Guillou, N.; Lamberti, C.; Bordiga, S.; Lillerud, K. P. A New Zirconium Inorganic Building Brick Forming Metal Organic Frameworks with Exceptional Stability J. Am. Chem. Soc. 2008, 130, 13850-13851 10.1021/ja8057953
44. Blee, E.; Schuber, F. Regio-and Enantioselectivity of Soybean Fatty Acid Epoxide Hydrolase J. Biolog. Chem. 1992, 267, 11881-11887
45. Sheldon, R. A. Cross-Linked Enzyme Aggregates as Industrial Biocatalysts Org. Process Res. Dev. 2011, 15, 213-223 10.1021/op100289f
46. Hausdorf, S.; Wagler, J.r.; Moβig, R.; Mertens, F. O. Proton and Water Activity-Controlled Structure Formation in Zinc Carboxylate-Based Metal Organic Frameworks J. Phys. Chem. A 2008, 112, 7567-7576 10.1021/jp7110633
47. Yang, J.; Dai, Y.; Zhu, X.; Wang, Z.; Li, Y.; Zhuang, Q.; Shi, J.; Gu, J. Metal-Organic Frameworks with Inherent Recognition Sites for Selective Phosphate Sensing through Their Coordination-Induced Fluorescence Enhancement Effect J. Mater. Chem. A 2015, 3, 7445-7452 10.1039/C5TA00077G
48. Lei, H.; Wang, W.; Chen, L. L.; Li, X. C.; Yi, B.; Deng, L. The Preparation and Catalytically Active Characterization of Papain Immobilized on Magnetic Composite Microspheres Enzyme Microb. Technol. 2004, 35, 15-21 10.1016/j.enzmictec.2004.03.007
49. Talekar, S.; Ghodake, V.; Ghotage, T.; Rathod, P.; Deshmukh, P.; Nadar, S.; Mulla, M.; Ladole, M. Novel Magnetic Cross-Linked Enzyme Aggregates (Magnetic Cleas) of Alpha Amylase Bioresour. Technol. 2012, 123, 542-547 10.1016/j.biortech.2012.07.044
50. Wang, M.; Qi, W.; Yu, Q.; Su, R.; He, Z. Cross-Linking Enzyme Aggregates in the Macropores of Silica Gel: A Practical and Efficient Method for Enzyme Stabilization Biochem. Eng. J. 2010, 52, 168-174 10.1016/j.bej.2010.08.003
51. Yu, C.-Y.; Li, X.-F.; Lou, W.-Y.; Zong, M.-H. Cross-Linked Enzyme Aggregates of Mung Bean Epoxide Hydrolases: A Highly Active, Stable and Recyclable Biocatalyst for Asymmetric Hydrolysis of Epoxides J. Biotechnol. 2013, 166, 12-19 10.1016/j.jbiotec.2013.04.015
52. Lou, W.-Y.; Zong, M.-H.; Smith, T. J.; Wu, H.; Wang, J.-F. Impact of Ionic Liquids on Papain: An Investigation of Structure-Function Relationships Green Chem. 2006, 8, 509-512 10.1039/B600930A
53. Vecchio, G.; Zambianchi, F.; Zacchetti, P.; Secundo, F.; Carrea, G. Fourier-Transform Infrared Spectroscopy Study of Dehydrated Lipases from Candida Antarctica B and Pseudomonas Cepacia Biotechnol. Bioeng. 1999, 64, 545-551 10.1002/(SICI)1097-0290(19990905)64:5<545::AID-BIT4>3.0.CO;2-Y
54. Zaks, A.; Klibanov, A. M. Enzymatic Catalysis in Nonaqueous Solvents J. Biol. Chem. 1988, 263, 3194-3201
55. Klibanov, A. M. Improving Enzymes by Using Them in Organic Solvents Nature 2001, 409, 241-246 10.1038/35051719
56. Danson, M. J.; Hough, D. W. Structure, Function and Stability of Enzymes from the Archaea Trends Microbiol. 1998, 6, 307-314 10.1016/S0966-842X(98)01316-X
57. Kumar, V. V.; Kumar, M. P.; Thiruvenkadaravi, K.; Baskaralingam, P.; Kumar, P. S.; Sivanesan, S. Preparation and Characterization of Porous Cross Linked Laccase Aggregates for the Decolorization of Triphenyl Methane and Reactive Dyes Bioresour. Technol. 2012, 119, 28-34 10.1016/j.biortech.2012.05.078
58. Gorke, J. T.; Srienc, F.; Kazlauskas, R. J. Hydrolase-Catalyzed Biotransformations in Deep Eutectic Solvents Chem. Commun. 2008, 1235-1237 10.1039/b716317g