Citation: Attaullah Bukhari, Ani Idris, Madiha Atta, Teo Chee Loong. Covalent immobilization of Candida antarctica lipase B on nanopolystyrene and its application to microwave-assisted esterification[J]. Chinese Journal of Catalysis, ;2014, 35(9): 1555-1564. doi: 10.1016/S1872-2067(14)60111-X shu

Covalent immobilization of Candida antarctica lipase B on nanopolystyrene and its application to microwave-assisted esterification

1.
Department of Bioprocess Engineering, Faculty of Chemical Engineering, c/o Institute of Bioproduct Development, University Teknology Malaysia, 81310 UTM Skudai, Johor, Malaysia

Corresponding author: Ani Idris,
Received Date: 21 February 2014
Available Online: 14 April 2014

Nanopolystyrene was used as a solid support for the covalent immobilization of Candida antarctica lipase B (CalB) using the photoreactive reagent 1-fluoro-2-nitro-4-azido benzene (FNAB) as a coupling reagent. The obtained derivative was then used as a biocatalyst in a microwave assisted esterification experiment. Factors such as contact time, pH, and enzyme concentration were investigated during immobilization. The hydrolytic activity, thermal, and operational stability of immobilized-CalB were determined. The maximum immobilized yield (218 µg/mg support) obtained at pH 6.8 exhibited optimum hydrolytic activity (4.42 × 10³ mU p-nitrophenol/min). The thermal stability of CalB improved significantly when it was immobilized at pH 10, however, the immobilized yield was very low (93.6 µg/mg support). The immobilized-CalB prepared at pH 6.8 and pH 10 retained 50% of its initial activity after incubation periods of 14 and 16 h, respectively, at 60 ℃. The operational stability was investigated for the microwave assisted esterification of oleic acid with methanol. Immobilized-CalB retained 50% of its initial activity after 15 batch cycles in the microwave-assisted esterification. The esterification time was notably reduced under microwave irradiation. The combined use of a biocatalyst and microwave heating is thus an alternative total green synthesis process.
- Candida antarctica lipase B,
- 1-Fluoro-2-nitro-4-azido benzene,
- Covalent immobilization,
- Nanopolystyrene,
- Hydrolytic activity,
- Microwave assisted esterification
1. [1]
  [1] Clouthierz C M, Pelletier J N. Chem Soc Rev, 2012, 41: 1585
2. [2]
  [2] Salis A, Meloni D, Ligas S, Casula M F, Monduzzi M, Solinas V, Dumitriu E. Langmuir, 2005, 21: 5511
3. [3]
  [3] Rodrigues D S, Mendes A A, Adriano W S, Goncalves L R B, Giordano R L C. J Mol Catal B, 2008, 51: 100
4. [4]
  [4] Brigida A I S, Pinheiro A D T, Ferreira A L O, Pinto G A S, Goncalves L R B. Appl Biochem Biotechnol, 2007, 137: 67
5. [5]
  [5] Balcao V M, Paiva A L, Malcata F X. Enzyme Microb Technol, 1996, 18: 392
6. [6]
  [6] Sun J N, Jing Y J, Zhou L Y, Gao J. New Biotechnol, 2010, 27: 53
7. [7]
  [7] Zhao H, Song Z Y. Biochem Eng J, 2010, 49: 113
8. [8]
  [8] Idris A, Bukhari A. Biotechnol Adv, 2012, 30: 550
9. [9]
  [9] Mateo C, Abian O, Bernedo M, Cuenca E, Fuentes M, Fernandez-Lorente G, Palomo J M, Grazu V, Pessela B C C, Giacomini C, Irazoqui G, Villarino A, Ovsejevi K, Batista-Viera F, Fernandez-Lafuente R, Guisan J M. Enzym Microb Technol, 2005, 37: 456
10. [10]
  [10] Dai T H, Miletic N, Loos K, Elbahri M, Abetz V. Macromol Chem Phys, 2011, 212: 319
11. [11]
  [11] Boros Z, Weiser D, Markus M, Abahaziova E, Magyar A, Tomin A, Koczka B, Kovacs P, Poppe L. Proc Biochem, 2013, 48: 1039
12. [12]
  [12] Silva J A, Macedo G P, Rodrigues D S, Giordano R L C, Goncalves L R B. Biochem Eng J, 2012, 60: 16
13. [13]
  [13] Barbosa O, Ruiz M, Ortiz C, Fernandez M, Torres R, Fernandez-Lafuente R. Proc Biochem, 2012, 47: 867
14. [14]
  [14] Kim J, Grate J W, Wang P. Trends Biotechnol, 2008, 26: 639
15. [15]
  [15] Kim J, Grate J W, Wang P. Chem Eng Sci, 2006, 61: 1017
16. [16]
  [16] Lee S M, Jin L H, Kim J H, Han S O, Na H B, Hyeon T, Koo Y M, Kim J, Lee J H. Bioprocess Biosyst Eng, 2010, 33: 141
17. [17]
  [17] Fang Y, Huang X J, Chen P C, Xu Z K. BMB Reports, 2011, 44: 87
18. [18]
  [18] Jain S, Chattopadhyay S, Jackeray R, Abid C K V Z, Singh H. Nanoscale, 2013, 5: 6883
19. [19]
  [19] Kappe C O. Angew Chem Int Ed, 2004, 43: 6250
20. [20]
  [20] Nuchter M, Ondruschka B, Bonrath W, Gum A. Green Chem, 2006, 6: 141
21. [21]
  [21] Wu S S, Liu P, Leng Y, Wang J. Catal Lett, 2009, 132: 500
22. [22]
  [22] Xu L, Li J, Yang L N, Dong J L, Sun Y M. Int J Sci Eng Res, 2013, 4: 1909
23. [23]
  [23] Lucena I L, Silva G F, Fernandes F A N. Ind Eng Chem Res, 2008, 47: 6885
24. [24]
  [24] Bukhari A, Idris A, Atta M. Malay J Fund App Sci, 2014, 10: 28
25. [25]
  [25] Fleet G W J, Knowles J R, Porter R R. Biochem J, 1972, 128: 499
26. [26]
  [26] Miletic N, Abetz V, Ebert K, Loos K. Macromol Rapid Commun, 2010, 31: 71
27. [27]
  [27] Bradford M M. Anal Biochem, 1976, 72: 248
28. [28]
  [28] Miletic N, Nastasovic A, Loos K. Bioresour Technol, 2012, 115: 126
29. [29]
  [29] Ebrahimi S, Amini G, Younesi H, Ghasem DN. Mid-East J Sci Res, 2012, 11: 323
30. [30]
  [30] Shimada Y, Watanabe Y, Sugihara A, Tominaga Y. J Mol Catal B, 2002, 17: 133
31. [31]
  [31] Mei Y, Miller L, Gao W, Gross R A. Biomacomol, 2003, 4: 70
32. [32]
  [32] Mohy Eldin M S, El Enshasy H A, Hassan M E, Haroun B, Hassan E A. J Appl Polym Sci, 2012, 125: 3820
33. [33]
  [33] Ji P J, Atherton J H, Page M I. J Org Chem, 2011, 76: 3286
34. [34]
  [34] Wong LS, Khan F, Micklefield J. Chem Rev, 2009, 109: 4025
35. [35]
  [35] Adriano W S, Filho E H C, Silva J A, Giordano R L C, Goncalves L R B. Braz J Chem Eng, 2005, 22: 529
36. [36]
  [36] Pedroche J, Yust M M, Mateo C, Fernandez-Lafuente R, Julio G C, Alaiz M, Vioque J, Guisan J M, Millan F. Enzym Microb Technol, 2007, 40: 1160
37. [37]
  [37] Tee B L, Kaletunc G. Biotechnol Prog, 2009, 25: 436
38. [38]
  [38] Porcelli M, Cacciapuoti G, Fusco S, Massa R, dAmbrosio G, Bertoldo C, DeRosa M, Zappia V. Fed Eur Biochem Soc Lett, 1997, 402: 102
39. [39]
  [39] Deng L, Nie K L, Wang F, Tan T W. Chin J Chem Eng, 2005, 13: 529
40. [40]
  [40] Ros P C M, Castro H F, Carvalho A K F, Soares C M F, Moraes F F, Zanin G M. J Ind Microbiol Biotechnol, 2012, 39: 529
41. [41]
  [41] Rejasse B, Lamare S, Legoy M D, Besson T. Org Biomol Chem, 2004, 2: 1086
42. [42]
  [42] Di X W, Li N, Zhang J. Adv Mat Res, 2012, 354: 133
43. [43]
  [43] Li M, Chen D Y, Zhu X F. Chin J Catal (李明, 陈登宇, 朱锡锋. 催化学报), 2013, 34: 1674
1. [1]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
2. [2]
  Qinwen Zheng , Xin Liu , Lintao Tian , Yi Zhou , Libing Liao , Guocheng Lv . Mechanism of Fenton catalytic degradation of Rhodamine B induced by microwave and Fe₃O₄. Chinese Chemical Letters, 2025, 36(4): 109771-. doi: 10.1016/j.cclet.2024.109771
3. [3]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
4. [4]
  Miao-Miao Chen , Min-Ling Zhang , Xiao Song , Jun Jiang , Xiaoqian Tang , Qi Zhang , Xiuhua Zhang , Peiwu Li . Smartphone-assisted electrochemiluminescence imaging test strips towards dual-signal visualized and sensitive monitoring of aflatoxin B1 in corn samples. Chinese Chemical Letters, 2025, 36(1): 109785-. doi: 10.1016/j.cclet.2024.109785
5. [5]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
6. [6]
  Hong Dong , Feng-Ming Zhang . Covalent organic frameworks for artificial photosynthetic diluted CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(7): 100307-100307. doi: 10.1016/j.cjsc.2024.100307
7. [7]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
8. [8]
  Junhua Wang , Xin Lian , Xichuan Cao , Qiao Zhao , Baiyan Li , Xian-He Bu . Dual polarization strategy to enhance CH₄ uptake in covalent organic frameworks for coal-bed methane purification. Chinese Chemical Letters, 2024, 35(8): 109180-. doi: 10.1016/j.cclet.2023.109180
9. [9]
  Hang Chen , Chengzhi Cui , Hebo Ye , Hanxun Zou , Lei You . Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups. Chinese Chemical Letters, 2024, 35(5): 109145-. doi: 10.1016/j.cclet.2023.109145
10. [10]
  Rui Li , Ruijie Lu , Libin Yang , Jianwen Li , Zige Guo , Qiquan Yan , Mengjun Li , Yazhuo Ni , Keying Chen , Yaoyang Li , Bo Xu , Mengzhen Cui , Zhan Li , Zhiying Zhao . Immobilization of chitosan nano-hydroxyapatite alendronate composite microspheres on polyetheretherketone surface to enhance osseointegration by inhibiting osteoclastogenesis and promoting osteogenesis. Chinese Chemical Letters, 2025, 36(4): 110242-. doi: 10.1016/j.cclet.2024.110242
11. [11]
  Jiaqi Ma , Lan Li , Yiming Zhang , Jinjie Qian , Xusheng Wang . Covalent organic frameworks: Synthesis, structures, characterizations and progress of photocatalytic reduction of CO2. Chinese Journal of Structural Chemistry, 2024, 43(12): 100466-100466. doi: 10.1016/j.cjsc.2024.100466
12. [12]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
13. [13]
  Guang-Xu Duan , Queting Chen , Rui-Rui Shao , Hui-Huang Sun , Tong Yuan , Dong-Hao Zhang . Encapsulating lipase on the surface of magnetic ZIF-8 nanosphers with mesoporous SiO₂ nano-membrane for enhancing catalytic performance. Chinese Chemical Letters, 2025, 36(2): 109751-. doi: 10.1016/j.cclet.2024.109751
14. [14]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
15. [15]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
16. [16]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
17. [17]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
18. [18]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
19. [19]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
20. [20]
  Jun Xiong , Ke-Ke Chen , Neng-Bin Xie , Wei Chen , Wen-Xuan Shao , Tong-Tong Ji , Si-Yu Yu , Yu-Qi Feng , Bi-Feng Yuan . Demethylase-assisted site-specific detection of N¹-methyladenosine in RNA. Chinese Chemical Letters, 2024, 35(5): 108953-. doi: 10.1016/j.cclet.2023.108953

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(328)
HTML views(35)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142