Epoxidation of vinyl functionalized cubic Ia3d mesoporous silica for immobilization of penicillin G acylase

doi:10.1016/S1872-2067(14)60156-X

Abstract

Abstract:

Epoxy functionalized cubic Ia3d mesoporous silica (CIMS) was successfully synthesized by epoxidizing vinyl groups prepared on the CIMS by a co-condensation method. The synthesized material was characterized by X-ray diffraction, nitrogen sorption, transmission electron microscopy, thermogravimetric analysis, and solid state ¹³C NMR. The vinyl groups were found to be easily epoxidized to yield epoxy functionalized CIMS. The epoxy functionalized CIMS was used as a support for the immobilization of penicillin G acylase (PGA), and the effects of the epoxy group on the initial activity and the operational stability of the immobilized PGA were studied. The results showed that the enzyme loading and initial activity of the immobilized PGA decreased with increasing amounts of epoxy groups. These observations were due to a decrease in the pore size of the mesoporous silica as well as an increase in the hydrophobicity of the silica surface. However, an appropriate amount of epoxy groups on the CIMS support was found to improve the operational stability of the immobilized PGA. This improvement was the result of increased interactions between the epoxy functionalized CIMS support and the PGA.

Key words: Co-condensation method, Mesoporous silica, Enzyme, Immobilization, Penicillin G acylase

Wangcheng Zhan, Yongjun Lü, Ling Yang, Yanglong Guo, Yanqin Wang, Yun Guo, Guanzhong Lu. Epoxidation of vinyl functionalized cubic Ia3d mesoporous silica for immobilization of penicillin G acylase[J]. Chinese Journal of Catalysis, 2014, 35(10): 1709-1715.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60156-X

https://www.cjcatal.com/EN/Y2014/V35/I10/1709

References

[1] Bornscheuer U T. Angew Chem Int Ed, 2003, 42: 3336
[2] DiCosimo R, McAuliffe J, Poulose A J, Bohlmann G. Chem Soc Rev, 2013, 42: 6437
[3] Katchalski-Katzir E, Kraemer D M. J Mol Catal B, 2000, 10: 157
[4] Cao L Q. Curr Opin Chem Biol, 2005, 9: 217
[5] An Z, He J, Lu S, Yang L. AIChE J, 2010, 56: 2677
[6] Liese A, Hilterhaus L. Chem Soc Rev, 2013, 42: 6236
[7] Liu X H, Bu C H, Nan Z H, Zheng L C, Qiu Y, Lu X Q. Talanta, 2013, 105: 63
[8] He J, Song Z H, Ma H, Yang L, Guo C X. J Mater Chem, 2006, 16: 4307
[9] Yiu H H P, Wright P A. J Mater Chem, 2005, 15: 3690
[10] Hartmann M. Chem Mater, 2005, 17: 4577
[11] On D T, Desplantier-Giscard D, Danumah C, Kaliaguine S. Appl Catal A, 2001, 222: 299
[12] Hartmann M, Jung D. J Mater Chem, 2010, 20: 844
[13] Kim J, Grate J W, Wang P. Chem Eng Sci, 2006, 61: 1017
[14] Chong A S M, Zhao X S. Appl Surf Sci, 2004, 237: 398
[15] Yiu H H P, Wright P A, Botting N P. J Mol Catal B, 2001, 15: 81
[16] Wight A P, Davis M E. Chem Rev, 2002, 102: 3589
[17] Ispas C, Sokolov I, Andreescu S. Anal Boianal Chem, 2009, 393: 543
[18] Stein A, Melde B J, Schroden R C. Adv Mater, 2000, 12: 1403
[19] Burkett S L, Sims S D, Mann S. Chem Commun, 1996: 1367
[20] Macquarrie D J. Chem Commun, 1996: 1961
[21] Hoffmann F, Cornelius M, Morell J, Froba M. Angew Chem Int Ed, 2006, 45: 3216
[22] Lim M H, Stein A. Chem Mater, 1999, 11: 3285
[23] Sakaguchi K, Matsui M, Mizukami F. Appl Microbiol Biotechnol, 2005, 67: 306
[24] Miyahara M, Vinu A, Ariga K. J Nanosci Nanotechnol, 2006, 6: 1765
[25] Sheldon R A, van Pelt S. Chem Soc Rev, 2013, 42: 6223
[26] Sayari A, Hamoudi S. Chem Mater, 2001, 13: 3151
[27] Huh S, Wiench J W, Yoo J C, Pruski M, Lin V S Y. Chem Mater, 2003, 15: 4247
[28] MacLachlan M J, Asefa T, Ozin G A. Chem-Eur J, 2000, 6: 2507
[29] Wang J, Zou Y C, Sun Y, Hemgesberg M, Shffner D, Gao H C, Song X J, Zhang W X, Jia M J, Thiel W R. Chin J Catal (王静, 邹永存, 孙渝, Hemgeserg M, Shffner D, 高洪成, 宋晓静, 张文祥, 贾明君, Thiel W R. 催化学报), 2014, 35: 532
[30] Cai W J, Zhou Y, Bao R L, Yue B, He H Y. Chin J Catal (蔡雯佳, 周琰, 包任烈, 岳斌, 贺鹤勇. 催化学报), 2013, 34: 193
[31] Richer R. Chem Comm, 1998: 1775
[32] Hoffmann F, Cornelius M, Morell J, Froba M. J Nanosci Nanotechnol, 2006, 6: 265
[33] Mateo C, Fernandez-Lorente G, Abian O, Fernandez-Lafuente R, Guisan J M. Biomacromolecules, 2000, 1: 739
[34] Boller T, Meier C, Menzler S. Org Process Res Dev, 2002, 6: 509
[35] Lü Y J, Lu G Z, Wang Y Q, Guo Y L, Guo Y, Zhang Z G, Wang Y S, Liu X H. Adv Funct Mater, 2007, 17: 2160
[36] Xue P, Xu F, Xu L D. Appl Surf Sci, 2008, 255: 1625
[37] Wang Y Q, Zibrowius B, Yang C M, Spliethoff B, Schüth F. Chem Commun, 2004: 46
[38] Wang Y Q, Yang C M, Zibrowius B, Spliethoff B, Linden M, Schüth F. Chem Mater, 2003, 15: 5029
[39] Xia L Y, Zhang M Q, Rong M Z, Xu W M. Phys Chem Chem Phys, 2010, 12: 10569
[40] Schwartz N N, Blumbergs J H. J Org Chem, 1964, 29: 1976
[41] Asefa T, Kruk M, MacLachlan M J, Coombs N, Grondey H, Jaroniec M, Ozin G A. Adv Funct Mater, 2001, 11: 447
[42] Pang J B, Hampsey J E, Hu Q Y, Wu Z W, John V T, Lu Y F. Chem Commun, 2004: 682
[43] Ryoo R, Joo S H, Kim J M. J Phys Chem B, 1999, 103: 7435
[44] Kleitz F, Choi S H, Ryoo R. Chem Commun, 2003: 2136
[45] Xue P, Lu G Z, Guo Y L, Wang Y S, Guo Y. J Mol Catal B, 2004, 30: 75
[46] Yang C M, Zibrowius B, Schüth F. Chem Commun, 2003: 1772
[47] Yang C M, Zibrowius B, Schmidt W, Schüth F. Chem Mater, 2004, 16: 2918
[48] Yang C M, Smatt J H, Zibrowius B, Linden M. New J Chem, 2004, 28: 1520
[49] Webb P A, Orr C. Analytical Methods in Fine Particle Technology. Norcross: Micromertics Instrument Corporation, 1997. 53
[50] Shimada T, Aoki K, Shinoda Y, Nakamura T, Tokunaga N, Inagaki S, Hayashi T. J Am Chem Soc, 2003, 125: 4688
[51] Zhao X S, Lu G Q. J Phys Chem B, 1998, 102: 1556