Dual-Surface Functionalization of Metal-Organic Frameworks for Enhancing the Catalytic Activity of Candida antarctica Lipase B in Polar Organic Media

ACS Catalysis

Volumn 7, Issue 1, 2017, Pages 438-442

  Jung, Suhyun ^a   Park, Seongsoon ^a  

^a Sungshin Women's University   (South Korea)

Author keywords

bioconjugation; immobilization; lipase; metal organic frameworks; multifunctionalization; post synthetic modification; surface modification

Indexed keywords

ACETONITRILE; BIOCATALYSTS; CANDIDA; CARBOXYLATION; CRYSTALLINE MATERIALS; FATTY ACIDS; FUNCTIONAL MATERIALS; ISOMERS; LIPASES; MOLECULES; ORGANIC POLYMERS; ORGANIC SOLVENTS; ORGANOMETALLICS; RADIOACTIVE WASTE VITRIFICATION; SURFACE TREATMENT; YEAST;

BIO-CONJUGATION; CANDIDA ANTARCTICA LIPASE B; METAL ORGANIC FRAMEWORK; METALORGANIC FRAMEWORKS (MOFS); MULTI-FUNCTIONALIZATION; NONPOLAR ORGANIC SOLVENTS; POSTSYNTHETIC MODIFICATION; SURFACE FUNCTIONALIZATION;

CATALYST ACTIVITY;

EID: 85019743650     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.6b03222     Document Type: Article

References (57)

1. Wu, Q.; Soni, P.; Reetz, M. T. J. Am. Chem. Soc. 2013, 135, 1872-1881 10.1021/ja310455t
2. Naik, S.; Basu, A.; Saikia, R.; Madan, B.; Paul, P.; Chaterjee, R.; Brask, J.; Svendsen, A. J. Mol. Catal. B: Enzym. 2010, 65, 18-23 10.1016/j.molcatb.2010.01.002
3. Svedendahl, M.; Hult, K.; Berglund, P. J. Am. Chem. Soc. 2005, 127, 17988-17989 10.1021/ja056660r
4. Houde, A.; Kademi, A.; Leblanc, D. Appl. Biochem. Biotechnol. 2004, 118, 155-170 10.1385/ABAB:118:1-3:155
5. Kirk, O.; Christensen, M. W. Org. Process Res. Dev. 2002, 6, 446-451 10.1021/op0200165
6. Jaeger, K. E.; Dijkstra, B. W.; Reetz, M. T. Annu. Rev. Microbiol. 1999, 53, 315-351 10.1146/annurev.micro.53.1.315
7. Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, 2 nd Edition; Wiley-VCH: Weinheim, Germany, 2006.
8. Anderson, E. M.; Larsson, K. M.; Kirk, O. Biocatal. Biotransform. 1998, 16, 181-204 10.3109/10242429809003198
9. Frykman, H.; Öhrner, N.; Norin, T.; Hult, K. Tetrahedron Lett. 1993, 34, 1367-1370 10.1016/S0040-4039(00)91797-0
10. Koops, B. C.; Papadimou, E.; Verheij, H. M.; Slotboom, A. J.; Egmond, M. R. Appl. Microbiol. Biotechnol. 1999, 52, 791-796 10.1007/s002530051593
11. Arroyo, M.; Sanchez-Montero, J. M.; Sinisterra, J. V. Enzyme Microb. Technol. 1999, 24, 3-12 10.1016/S0141-0229(98)00067-2
12. Morgan, B.; Dodds, D. R.; Zaks, A.; Andrews, D. R.; Klesse, R. J. Org. Chem. 1997, 62, 7736-7743 10.1021/jo9709920
13. Martinelle, M.; Hult, K. Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1995, 1251, 191-197 10.1016/0167-4838(95)00096-D
14. Laane, C.; Boeren, S.; Vos, K.; Veeger, C. Biotechnol. Bioeng. 1987, 30, 81-87 10.1002/bit.260300112
15. Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395-8401 10.1021/jo015761e
16. Fitzpatrick, P. A.; Steinmetz, A. C. U.; Ringe, D.; Klibanov, A. M. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 8653-8657 10.1073/pnas.90.18.8653
17. de Albuquerque, T. L.; Rueda, N.; dos Santos, J. C. S.; Barbosa, O.; Ortiz, C.; Binay, B.; Özdemir, E.; Gonçalves, L. R. B.; Fernandez-Lafuente, R. Process Biochem. 2016, 51, 865-874 10.1016/j.procbio.2016.04.002
18. dos Santos, J. C. S.; Rueda, N.; Gonçalves, L. R. B.; Fernandez-Lafuente, R. Enzyme Microb. Technol. 2015, 77, 1-7 10.1016/j.enzmictec.2015.05.001
19. Jiang, J.; Zhao, Y.; Yaghi, O. M. J. Am. Chem. Soc. 2016, 138, 3255-3265 10.1021/jacs.5b10666
20. Zhou, H.-C.; Kitagawa, S. Chem. Soc. Rev. 2014, 43, 5415-5418 10.1039/C4CS90059F
21. Furukawa, H.; Cordova, K. E.; O'Keeffe, M.; Yaghi, O. M. Science 2013, 341, 1230444 10.1126/science.1230444
22. Zhou, H.-C.; Long, J. R.; Yaghi, O. M. Chem. Rev. 2012, 112, 673-674 10.1021/cr300014x
23. Cui, Y.; Li, B.; He, H.; Zhou, W.; Chen, B.; Qian, G. Acc. Chem. Res. 2016, 49, 483-493 10.1021/acs.accounts.5b00530
24. Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196-1231 10.1021/cr2003147
25. Suh, M. P.; Park, H. J.; Prasad, T. K.; Lim, D. W. Chem. Rev. 2012, 112, 782-835 10.1021/cr200274s
26. Li, J.-R.; Sculley, J.; Zhou, H.-C. Chem. Rev. 2012, 112, 869-932 10.1021/cr200190s
27. Banerjee, R.; Phan, A.; Wang, B.; Knobler, C.; Furukawa, H.; O'Keeffe, M.; Yaghi, O. M. Science 2008, 319, 939-943 10.1126/science.1152516
28. Ma, S.; Sun, D.; Simmons, J. M.; Collier, C. D.; Yuan, D.; Zhou, H.-C. J. Am. Chem. Soc. 2008, 130, 1012-1016 10.1021/ja0771639
29. Matsuda, R.; Kitaura, R.; Kitagawa, S.; Kubota, Y.; Belosludov, R. V.; Kobayashi, T. C.; Sakamoto, H.; Chiba, T.; Takata, M.; Kawazoe, Y.; Mita, Y. Nature 2005, 436, 238-241 10.1038/nature03852
30. Millward, A. R.; Yaghi, O. M. J. Am. Chem. Soc. 2005, 127, 17998-17999 10.1021/ja0570032
31. Rowsell, J. L. C.; Yaghi, O. M. Angew. Chem., Int. Ed. 2005, 44, 4670-4679 10.1002/anie.200462786
32. Kitagawa, S.; Kitaura, R.; Noro, S.-I. Angew. Chem., Int. Ed. 2004, 43, 2334-2375 10.1002/anie.200300610
33. Rowsell, J. L. C.; Millward, A. R.; Park, K. S.; Yaghi, O. M. J. Am. Chem. Soc. 2004, 126, 5666-5667 10.1021/ja049408c
34. Rosi, N. L.; Eckert, J.; Eddaoudi, M.; Vodak, D. T.; Kim, J.; O'Keeffe, M.; Yaghi, O. M. Science 2003, 300, 1127-1129 10.1126/science.1083440
35. Férey, G.; Latroche, M.; Serre, C.; Millange, F.; Loiseau, T.; Percheron-Gugan, A. Chem. Commun. 2003, 2976-2977 10.1039/B308903G
36. Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keeffe, M.; Yaghi, O. M. Science 2002, 295, 469-472 10.1126/science.1067208
37. Thacker, N. C.; Lin, Z.; Zhang, T.; Gilhula, J. C.; Abney, C. W.; Lin, W. J. Am. Chem. Soc. 2016, 138, 3501-3509 10.1021/jacs.5b13394
38. Evans, J. D.; Sumby, C. J.; Doonan, C. J. Chem. Soc. Rev. 2014, 43, 5933-5951 10.1039/C4CS00076E
39. Babarao, R.; Coghlan, C. J.; Rankine, D.; Bloch, W. M.; Gransbury, G. K.; Sato, H.; Kitagawa, S.; Sumby, C. J.; Hill, M. R.; Doonan, C. J. Chem. Commun. 2014, 50, 3238-3241 10.1039/c4cc00700j
40. Cohen, S. M. Chem. Rev. 2012, 112, 970-1000 10.1021/cr200179u
41. Yamada, T.; Kitagawa, H. J. Am. Chem. Soc. 2009, 131, 6312-6313 10.1021/ja809352y
42. Taylor-Pashow, K. M. L.; Rocca, J. D.; Xie, Z.; Tran, S.; Lin, W. J. Am. Chem. Soc. 2009, 131, 14261-14263 10.1021/ja906198y
43. Wang, Z.; Cohen, S. M. Angew. Chem., Int. Ed. 2008, 47, 4699-4702 10.1002/anie.200800686
44. Tanabe, K. K.; Wang, Z.; Cohen, S. M. J. Am. Chem. Soc. 2008, 130, 8508-8517 10.1021/ja801848j
45. Ingleson, M. J.; Perez Barrio, J.; Guilbaud, J.-B.; Khimyak, Y. Z.; Rosseinsky, M. J. Chem. Commun. 2008, 2680-2682 10.1039/b718367d
46. Burrows, A. D.; Frost, C. G.; Mahon, M. F.; Richardson, C. Angew. Chem., Int. Ed. 2008, 47, 8482-8486 10.1002/anie.200802908
47. Gadzikwa, T.; Lu, V.; Stern, C. L.; Wilson, S. R.; Hupp, J. T.; Nguyen, S. T. Chem. Commun. 2008, 5493-5495 10.1039/b805101a
48. Wang, Z.; Cohen, S. M. J. Am. Chem. Soc. 2007, 129, 12368-12369 10.1021/ja074366o
49. Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982-986 10.1038/35010088
50. Jung, S.; Kim, Y.; Kim, S.-J.; Kwon, T.-W.; Huh, S.; Park, S. Chem. Commun. 2011, 47, 2904-2906 10.1039/c0cc03288c
51. E is the enantiomeric ratio, as defined by: Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299 10.1021/ja00389a064
52. Reichardt, C. Solvent and Solvent Effects in Organic Chemistry, 3 rd Edition; Wiley-VCH: Weinheim, Germany, 2003; pp 472-474.
53. Schaate, A.; Roy, P.; Godt, A.; Lippke, J.; Waltz, F.; Wiebcke, M.; Behrens, P. Chem.-Eur. J. 2011, 17, 6643-6651 10.1002/chem.201003211
54. Sim, Y. K.; Jung, S.; Lim, J. Y.; Kim, J.; Kim, S.-H.; Song, B. K.; Kim, B. T.; Lee, H.; Park, S. Tetrahedron Lett. 2011, 52, 1041-1043 10.1016/j.tetlet.2010.12.099
55. Jung, S.; Park, S. Biotechnol. Lett. 2008, 30, 717-722 10.1007/s10529-007-9591-3
56. Rotticci, D.; Norin, T.; Hult, K. Org. Lett. 2000, 2, 1373-1376 10.1021/ol005639m
57. Mehta, J.; Bhardwaj, N.; Bhardwaj, S. K.; Kim, K.-H.; Deep, A. Coord. Chem. Rev. 2016, 322, 30-40 10.1016/j.ccr.2016.05.007