Covalent Organic Frameworks(COFs) Materials in Enzyme Immobilization and Mimic Enzymes

doi:10.7536/PC191226

Covalent organic frameworks(COFs) are a class of crystalline porous organic material, constructed with light elements by reversible covalent bonds. Due to their high surface area, low density, regular channel structure and facile functionalization, COFs have attracted much attention and shown high perspectives in gas adsorption, chemical sensing, heterogeneous catalysis, etc. Recently, COFs have shown potential applications in enzyme immobilization and mimic enzymes. COFs present an attractive category of enzyme immobilization matrix, because the functional groups on COFs can be readily tailored to hold specific interactions between COFs and enzymes. Moreover, the continuous and confined open channels of COFs provide a favorable micro-environment for infiltrating enzymes. Meanwhile, the mimic enzyme features of COFs are explored, COF mimic enzymes are designed either by “from bottom to top” method or post modification strategy. As a result, not only the carrier materials for enzyme immobilization are expanded, but also it provides new ideas for biomimetic catalysis of mimic enzymes. This review focuses on recent advances of COFs immobilized enzyme and COFs mimic enzymes(nanozyme) applied in biocatalysis. Special emphasis is placed on the deliberation of synthetic and functional strategies, immobilization methods of COFs carrier, as well as the design concept, catalytic activity and selectivity of COFs mimic enzymes. Finally, the remaining challenges of COFs in enzyme catalysis and prospects in this field are summarized.

Contents

1 Introduction

2 Application of COFs materials in enzyme catalysis

2.1 COFs as immobilized enzyme carriers

2.2 COFs as mimic enzymes

3 Conclusion and outlook

Key words: covalent organic framework(COFs), composite material, enzyme immobilization, mimic enzyme, heterogeneous catalysis

Fig.1 The synthetic procedure for COF-ETTA- EDDA[37]

Fig.2 Synthesis of CON(TpBD)[41]

Fig.3 (a) Synthesis reaction of COF 1;(b) Illustration of the covalent strategy to bond various biomolecules with COFs[47]

Fig.4 (a) Preparation of SNW-1;(b) Fabrication of cellulase@poly(GMA-EDMA-SNW-1) capillary monolithic column[48]

Table 1 Textural parameters of various porous materials before and after loading of lipase PS as well as the corresponding loading capacity[29]

Materials	BET(m²·g^-1)	Loading capacity (mg·mg^-1)
COF-OH	1620	/
lipase@COF-OH	756	0.75
COF-ONa	1492	/
lipase@COF-ONa	854	0.59
POP-OMe	1056	/
lipase@POP-OMe	605	0.58
POP-V	952	/
lipase@POP-V	585	0.50
MCM-41	1008	/
lipase@MCM-41	712	0.35
PCN-128	2680	/
lipase@PCN-128	1295	0.64

Table 1 Textural parameters of various porous materials before and after loading of lipase PS as well as the corresponding loading capacity[29]

Materials	BET(m²·g^-1)	Loading capacity (mg·mg^-1)
COF-OH	1620	/
lipase@COF-OH	756	0.75
COF-ONa	1492	/
lipase@COF-ONa	854	0.59
POP-OMe	1056	/
lipase@POP-OMe	605	0.58
POP-V	952	/
lipase@POP-V	585	0.50
MCM-41	1008	/
lipase@MCM-41	712	0.35
PCN-128	2680	/
lipase@PCN-128	1295	0.64

Fig.5 Schematic illustration of ETTA-TPAL synthesis and the assembly of both GOD and MP-11 into the pores of COFETTA-TPAL[49]

Fig.6 2D COFs containing iron porphyrin used as biomimetic oxidation catalyst[51]

Table 2 Kinetic parameters for the oxidation of substrates by different catalysts[51]

Substrate	Catalyst	k _cat(min^-1)	K _m(mM)	k _cat/K _m(M^-1·min^-1)	ref
ABTS	CHF-1	0.45	0.022	2.06×10⁴	51
	FeTPPCL	3.67	0.0055	6.62×10⁵
	HRP	887.54	0.15	5.94×10⁶	52
THB	HRP	887.54	0.15	5.94×10⁶	52
	CHF-1	0.33	0.0040	8.26×10⁴
	HRP	1965	0.89	2.2×10⁶
	hemin-graphene	246	1.22	2.0×10⁵
	FeTMPyP-graphene	545	0.96	5.7×10⁵
	PCN-222(Fe)	16.1	0.33	4.85×10⁴	53

Table 2 Kinetic parameters for the oxidation of substrates by different catalysts[51]

Substrate	Catalyst	k _cat(min^-1)	K _m(mM)	k _cat/K _m(M^-1·min^-1)	ref
ABTS	CHF-1	0.45	0.022	2.06×10⁴	51
	FeTPPCL	3.67	0.0055	6.62×10⁵
	HRP	887.54	0.15	5.94×10⁶	52
THB	HRP	887.54	0.15	5.94×10⁶	52
	CHF-1	0.33	0.0040	8.26×10⁴
	HRP	1965	0.89	2.2×10⁶
	hemin-graphene	246	1.22	2.0×10⁵
	FeTMPyP-graphene	545	0.96	5.7×10⁵
	PCN-222(Fe)	16.1	0.33	4.85×10⁴	53

Fig.7 Illustration of the trimerization of DCB to yield CTF-1 by using a microwave-enhanced high-temperature ionothermal method[35]

Table 3 Comparison of the steady-state kinetic fitting parameters V max and K m[24]

Catalyst	K _m(mM)		V _max(M·s^-1)		ref
Catalyst	TMB	H₂O₂	TMB	H₂O₂	ref
Fe-COF	0.02	0.143	3.83×10^-8	4.74×10^-8	24
MIL-53(Fe)	1.08	0.04	8.78×10^-8	1.86×10^-8	34
HRP	0.434	3.7	1.0×10^-7	8.71×10^-8	56
Fe₃O₄@MIL-100(Fe)	0.112	0.077	1.14×10^-7	1.8×10^-7	57
CuNPs@C	1.65	1.89	1.21×10^-7	5.3×10^-8	58

Table 3 Comparison of the steady-state kinetic fitting parameters V max and K m[24]

Catalyst	K _m(mM)		V _max(M·s^-1)		ref
Catalyst	TMB	H₂O₂	TMB	H₂O₂	ref
Fe-COF	0.02	0.143	3.83×10^-8	4.74×10^-8	24
MIL-53(Fe)	1.08	0.04	8.78×10^-8	1.86×10^-8	34
HRP	0.434	3.7	1.0×10^-7	8.71×10^-8	56
Fe₃O₄@MIL-100(Fe)	0.112	0.077	1.14×10^-7	1.8×10^-7	57
CuNPs@C	1.65	1.89	1.21×10^-7	5.3×10^-8	58

Fig.8 Colorimetric sensor for glucose detection using the Fe-COF as the catalyst[24]

Fig.9 PTAZo-Au for colorimetric detection of H2+ [59]

Table 4 Comparison of detection performances of PTAZo-Au and other materials[59]

Material	Method	Linear range(nM)	Detection limit(nM)	ref
PTAZo-Au	colorimetric	5~300	0.75	59
Rox-DNA functionalized silicon nanodots	fluorescence	10~1500	9.2	60
DNA-templated quantum dots	phosphorescence	20~800	4.8	61
AuNPs	colorimetric	1~600	0.3	62
COF-LZU8	fluorescence	250~1000	125	63

Table 4 Comparison of detection performances of PTAZo-Au and other materials[59]

Material	Method	Linear range(nM)	Detection limit(nM)	ref
PTAZo-Au	colorimetric	5~300	0.75	59
Rox-DNA functionalized silicon nanodots	fluorescence	10~1500	9.2	60
DNA-templated quantum dots	phosphorescence	20~800	4.8	61
AuNPs	colorimetric	1~600	0.3	62
COF-LZU8	fluorescence	250~1000	125	63

Fig.10 Synthesis of the copper-modified covalent triazine framework(CCTF)[64]

Table 5 Comparison of several colorimetric methods for Cu2+detection[65]

Catalyst	Linear range	LOD	ref
CTF	1.0~80 μg/L(15.75 nM~1.26 mM)	0.08 μg/L(1.25 nM)	65
Br-PEI-AuNPs	0.1~10 μM	0.03 μM	66
ZnO@ZnS core-shell nanoparticles	15~1500 μM	15 μM	67
Au@Pt nanohybrids	0.02~0.5 μM	4.0 nM	68
MOF(UIO-66)	0.00157~0.15737 μM	7.8 nM	69
TiO₂	16.2 nM~0.98 mM	16.2 nM	70

Table 5 Comparison of several colorimetric methods for Cu2+detection[65]

Catalyst	Linear range	LOD	ref
CTF	1.0~80 μg/L(15.75 nM~1.26 mM)	0.08 μg/L(1.25 nM)	65
Br-PEI-AuNPs	0.1~10 μM	0.03 μM	66
ZnO@ZnS core-shell nanoparticles	15~1500 μM	15 μM	67
Au@Pt nanohybrids	0.02~0.5 μM	4.0 nM	68
MOF(UIO-66)	0.00157~0.15737 μM	7.8 nM	69
TiO₂	16.2 nM~0.98 mM	16.2 nM	70

Fig.11 Synthesis of AuNPs@Tp-Bpy[72]

[1]	丁慧敏(Ding H M), 喻娜(Yu N), 汪成(Wang C) . 中国科学:化学 (Scientia Sinica Chimica), 2016,46(7):625.
[2]	Ennaert T , Aelst J V , Dijkmans J , Clercq R D , Schutyser W , Dusselier M , Verboekend D , Sels B F . Chem. Soc. Rev., 2016,45:584. doi: 10.1039/c5cs00859j https://www.ncbi.nlm.nih.gov/pubmed/26691750 pmid: 26691750
[3]	Cui Y J , Li B , He H J , Zhou W , Chen B L , Qian G D . Acc. Chem. Res., 2016,49:483. https://www.ncbi.nlm.nih.gov/pubmed/26878085 pmid: 26878085
[4]	Das S , Heasman P , Ben T , Qiu S L . Chem. Rev., 2017,117:1515. https://www.ncbi.nlm.nih.gov/pubmed/28035812 pmid: 28035812
[5]	Tan L X , Tan B . Chem. Soc. Rev., 2017,46:3322. doi: 10.1039/c6cs00851h https://www.ncbi.nlm.nih.gov/pubmed/28224148 pmid: 28224148
[6]	Bezzu C G , Carta M , Tonkins A , Jansen J C , Bernardo P , Bazzarelli F , McKeown N B . Adv. Mater., 2012,24:5930. doi: 10.1002/adma.201202393 https://www.ncbi.nlm.nih.gov/pubmed/22961917 pmid: 22961917
[7]	Du R , Zheng Z , Mao N , Zhang N , Hu W P , Zhang J . Adv. Sci., 2015,2:1400006. doi: 10.1002/advs.201400006 http://doi.wiley.com/10.1002/advs.201400006
[8]	Ben T , Ren H , Ma S , Cao D , Lan J , Jing X , Wang W , Xu J , Deng F , Simmons J M , Qiu S , Zhu G . Angew. Chem. Int. Ed., 2009,48:9457. doi: 10.1002/anie.200904637 http://doi.wiley.com/10.1002/anie.200904637
[9]	Kuhn P , Antonietti M , Thomas A . Angew. Chem. Int. Ed., 2008,47:3450. doi: 10.1002/(ISSN)1521-3773 http://doi.wiley.com/10.1002/%28ISSN%291521-3773
[10]	Ding S Y , Wang W . Chem. Soc. Rev., 2013,42:548. doi: 10.1039/c2cs35072f https://www.ncbi.nlm.nih.gov/pubmed/23060270 pmid: 23060270
[11]	Feng X , Ding X S , Jiang D L . Chem. Soc. Rev., 2012,41:6010. doi: 10.1039/c2cs35157a https://www.ncbi.nlm.nih.gov/pubmed/22821129 pmid: 22821129
[12]	周婷(Zhou T), 龚祎凡(Gong Y F), 郭佳(Guo J) . 功能高分子学报 (Journal of Functional Polymers), 2018,31(3):189.
[13]	Côté A P , Benin A I , Ockwig N W , O’Keeffe M , Matzger A J , Yaghi O M . Science, 2005,310:1166. https://www.ncbi.nlm.nih.gov/pubmed/16293756 pmid: 16293756
[14]	Nagai A , Guo Z Q , Feng X , Jin S B , Chen X , Ding X S , Jiang D L . Nat. Commun., 2011,2:536. doi: 10.1038/ncomms1542 https://www.ncbi.nlm.nih.gov/pubmed/22086337 pmid: 22086337
[15]	Uribe-Romo F J , Hunt J R , Furukawa H , Klock C , O’Keeffe M , Yaghi O M . J. Am. Chem. Soc., 2009,131:4570. https://www.ncbi.nlm.nih.gov/pubmed/19281246 pmid: 19281246
[16]	Chan-Thaw C E , Villa A , Prati L , Thomas A . Chem. Eur. J., 2011,17:1052. https://www.ncbi.nlm.nih.gov/pubmed/21226123 pmid: 21226123
[17]	El-Kaderi H M , Hunt J R , Mendoza-Cortés J L , Côté A P , Taylor R E , O’Keeffe M , Yaghi O M . Science, 2007,316:268. doi: 10.1126/science.1139915 https://www.ncbi.nlm.nih.gov/pubmed/17431178 pmid: 17431178
[18]	Ding S Y , Gao J , Wang Q , Zhang Y , Song W G , Su C Y , Wang W . J. Am. Chem. Soc., 2011,133:19816. doi: 10.1021/ja206846p 53aebe2e-129c-4963-95b4-c62a0c87a2d0 http://dx.doi.org/10.1021/ja206846p
[19]	Furukawa H , Yaghi O M . J. Am. Chem. Soc., 2009,131:8875. https://www.ncbi.nlm.nih.gov/pubmed/19496589 pmid: 19496589
[20]	Wan S , Guo J , Kim J , Ihee H , Jiang D L . Angew. Chem. Int. Ed., 2009,48:5439. doi: 10.1002/anie.v48:30 http://doi.wiley.com/10.1002/anie.v48%3A30
[21]	Schmid A , Dordick J S , Hauer B , Kiener A , Wubbolts M , Witholt B . Nature, 2001,409:258. https://www.ncbi.nlm.nih.gov/pubmed/11196655 pmid: 11196655
[22]	Mohamad N R , Marzuki N H C , Buang N A , Huyop F, Wahab R A . Biotechnol Biotec Eq., 2015,29:205. doi: 10.1080/13102818.2015.1008192 http://www.tandfonline.com/doi/abs/10.1080/13102818.2015.1008192
[23]	Wang Q Q , Wei H , Zhang Z Q , Wang E , Dong S J . Trac-Trend. Anal. Chem., 2018,105:218. doi: 10.1016/j.trac.2018.05.012 https://linkinghub.elsevier.com/retrieve/pii/S0165993617304752
[24]	Wang J N , Yang X , Wei T X , Bao J C , Zhu Q S , Dai Z H . ACS Appl. Bio Mater., 2018,1:382. doi: 10.1021/acsabm.8b00104 https://pubs.acs.org/doi/10.1021/acsabm.8b00104
[25]	Mateo C , Palomo J M , Fernandez-Lorente G , Guisan J M , Fernandez-Lafuente R . Enzyme Microb. Tech., 2007,40:1451. doi: 10.1016/j.enzmictec.2007.01.018 https://linkinghub.elsevier.com/retrieve/pii/S0141022907000506
[26]	Rodrigues R C , Ortiz C , Berenguer-Murcia A , Torres R , Fernandez-Lafuente R . Chem. Soc. Rev., 2013,42:6290. https://www.ncbi.nlm.nih.gov/pubmed/23059445 pmid: 23059445
[27]	Vinu A , Murugesan V , Tangermann O , Hartmann M . Chem. Mater., 2004,16:3056. doi: 10.1021/cm049718u https://pubs.acs.org/doi/10.1021/cm049718u
[28]	Song Y P , Sun Q , Aguila B , Ma S Q . Adv. Sci., 2018,10:1002.
[29]	Sun Q , Fu C W , Aguila B , Perman J , Wang S , Huang H Y , Xiao S F , Ma S Q . J. Am. Chem. Soc., 2018,140:984. doi: 10.1021/jacs.7b10642 https://www.ncbi.nlm.nih.gov/pubmed/29275637 pmid: 29275637
[30]	Gao L Z , Zhuang J , Nie L , Zhang J B , Zhang Y , Gu N , Wang T H , Feng J , Yang D L , Perrett S , Yan X Y . Nat. Nanotechnol., 2007,2:577. https://www.ncbi.nlm.nih.gov/pubmed/18654371 pmid: 18654371
[31]	Wang S , Chen W , Liu A L , Hong L , Deng H H , Lin X H . ChemPhysChem, 2012,13:1199. https://www.ncbi.nlm.nih.gov/pubmed/22383315 pmid: 22383315
[32]	Lin Y H , Ren J S , Qu X G . Adv. Mater., 2014,26:4200. doi: 10.1002/adma.201400238 ce451c9f-9fa9-47ab-98ae-686650e61518 http://dx.doi.org/10.1002/adma.201400238
[33]	Song Y J , Qu K G , Zhao C , Ren J S , Qu X G . Adv. Mater., 2010,22:2206. doi: 10.1002/adma.200903783 https://www.ncbi.nlm.nih.gov/pubmed/20564257 pmid: 20564257
[34]	Ai L H , Li L L , Zhang C H , Fu J , Jiang J . Chem. Eur. J., 2013,19:15105. doi: 10.1002/chem.201303051 https://www.ncbi.nlm.nih.gov/pubmed/24150880 pmid: 24150880
[35]	He J , Xu F J , Hu J , Wang S L , Hou X D , Long Z . Microchem. J., 2017,135:91. doi: 10.1016/j.microc.2017.08.009 https://linkinghub.elsevier.com/retrieve/pii/S0026265X17307701
[36]	Kandambeth S , Venkatesh V , Shinde D B , Kumari S , Halder A , Verma S , Banerjee R . Nat. Commun., 2015,6:6786. doi: 10.1038/ncomms7786 https://www.ncbi.nlm.nih.gov/pubmed/25858416 pmid: 25858416
[37]	Sun Q , Aguila B , Lan P C , Ma S Q . Adv. Mater., 2019,31:1900008. doi: 10.1002/adma.v31.19 https://onlinelibrary.wiley.com/toc/15214095/31/19
[38]	Su D , Feng B , Xu P , Zeng Q , Shan B , Song Y G . Anal. Methods., 2018,10:4320. doi: 10.1039/C8AY01386A http://xlink.rsc.org/?DOI=C8AY01386A
[39]	Ni T H , Zhang D W , Wang J , Wang S , Liu H L , Sun B G . Sensor. Actuat. B-Chem., 2018,269:340. doi: 10.1016/j.snb.2018.04.172 https://linkinghub.elsevier.com/retrieve/pii/S0925400518308864
[40]	Li Z , Yang Y W . J. Mater. Chem. B, 2017,5:9278. doi: 10.1039/c7tb02647a https://www.ncbi.nlm.nih.gov/pubmed/32264531 pmid: 32264531
[41]	Kong W F , Wan J X , Namuangruk S , Guo J , Wang C C . Sci. Rep., 2018,8:5529. doi: 10.1038/s41598-018-23744-1 https://www.ncbi.nlm.nih.gov/pubmed/29615680 pmid: 29615680
[42]	Su L J , Zhang Z , Xiong Y H . Nanoscale, 2018,10:20120. https://www.ncbi.nlm.nih.gov/pubmed/30376033 pmid: 30376033
[43]	Wang H P , Jiao F L , Gao F Y , Zhao X Y , Zhao Y , Shen Y H , Zhang Y J , Qian X H . Anal. Bioanal. Chem., 2017,409:2179. doi: 10.1007/s00216-016-0163-z https://www.ncbi.nlm.nih.gov/pubmed/28078417 pmid: 28078417
[44]	Shi C , Deng C , Li Y , Zhang X , Yang P . Proteomics., 2014,14:1457. doi: 10.1002/pmic.201300487 https://www.ncbi.nlm.nih.gov/pubmed/24723515 pmid: 24723515
[45]	Zhao M , Zhang X , Deng C . Chem. Commun., 2015,51:8116. doi: 10.1039/C5CC01908G http://xlink.rsc.org/?DOI=C5CC01908G
[46]	Cheng G , Chen P , Wang Z G , Sui X J , Zhang J L , Ni J Z . Anal. Chim. Acta, 2014,812:65. doi: 10.1016/j.aca.2013.12.035 https://www.ncbi.nlm.nih.gov/pubmed/24491766 pmid: 24491766
[47]	Zhang S N , Zheng Y L , An H D , Aguila B , Yang C X , Dong Y Y , Xie W , Cheng P , Zhang Z J , Chen Y , Ma S Q . Angew. Chem. Int. Ed., 2018,57:16754. doi: 10.1002/anie.v57.51 https://onlinelibrary.wiley.com/toc/15213773/57/51
[48]	Xu S J , Wang Y Y , Li W , Ji Y B . J. Chromatogr. A, 2019,1602:481. https://www.ncbi.nlm.nih.gov/pubmed/31230876 pmid: 31230876
[49]	Wang L , Liang H H , Xu M L , Wang L Y , Xie Y , Song Y H . Sensor. Actuat. B-Chem., 2019,298:126859. doi: 10.1016/j.snb.2019.126859 https://linkinghub.elsevier.com/retrieve/pii/S0925400519310585
[50]	Wang K , Qi D D , Li Y L , Wang T Y , Liu H B , Jiang J Z . Coordin. Chem. Rev., 2017,378:188. doi: 10.1016/j.ccr.2017.08.023 https://linkinghub.elsevier.com/retrieve/pii/S0010854517304010
[51]	Wang X S , Chrzanowski M , Yuan D Q , Sweeting B S , Ma S Q . Chem. Mater., 2014,26:1639. doi: 10.1021/cm403860t https://pubs.acs.org/doi/10.1021/cm403860t
[52]	Xue T , Jiang S , Qu Y , Su Q , Cheng R , Dubin S , Chiu C Y , Kaner R , Huang Y , Duan X . Angew. Chem. Int. Ed., 2012,51:3822. doi: 10.1002/anie.v51.16 http://doi.wiley.com/10.1002/anie.v51.16
[53]	Feng D , Gu Z Y , Li J R , Jiang H L , Wei Z , Zhou H C . Angew. Chem. Int. Ed., 2012,51:10307. doi: 10.1002/anie.201204475 http://doi.wiley.com/10.1002/anie.201204475
[54]	Kuhn P , Antonietti M , Thomas A . Angew. Chem. Int. Ed., 2008,47:3450. doi: 10.1002/(ISSN)1521-3773 http://doi.wiley.com/10.1002/%28ISSN%291521-3773
[55]	Artz J . ChemCatChem., 2018,10:1753. doi: 10.1002/cctc.v10.8 http://doi.wiley.com/10.1002/cctc.v10.8
[56]	Dong, Y M , Zhang J J , Jiang P P , Wang G L , Wu X M , Zhao H , Zhang C . New J. Chem., 2015,39:4141. doi: 10.1039/C5NJ00012B http://xlink.rsc.org/?DOI=C5NJ00012B
[57]	Wu Y Z , Ma Y J , Xu G H , Wei F D , Ma Y S , Song Q , Wang X , Tang T , Song Y Y , Shi M L , Xu X M , Hu Q . Sensor. Actuat. B-Chem., 2017,249:195. doi: 10.1016/j.snb.2017.03.145 https://linkinghub.elsevier.com/retrieve/pii/S0925400517305737
[58]	Tan H L , Ma C J , Gao L , Li Q , Song Y H , Xu F G , Wang T , Wang L . Chem. Eur. J., 2014,20:16377. https://www.ncbi.nlm.nih.gov/pubmed/25332148 pmid: 25332148
[59]	Li W , Li Y , Qian H L , Zhao X , Yang C X , Yan X P . Talanta, 2019,204:224. doi: 10.1016/j.talanta.2019.05.086 https://www.ncbi.nlm.nih.gov/pubmed/31357286 pmid: 31357286
[60]	Zhang Y A , Guo S , Jiang Z R , Mao G B , Ji X H , He Z K . Anal. Chem., 2018,90:9796. doi: 10.1021/acs.analchem.8b01574 https://www.ncbi.nlm.nih.gov/pubmed/30014694 pmid: 30014694
[61]	Miao Y M , Sun X J , Lv J Z , Yan G Q . Anal. Chem., 2019,91:5036. doi: 10.1021/acs.analchem.8b05099 https://www.ncbi.nlm.nih.gov/pubmed/30919612 pmid: 30919612
[62]	Long Y J , Li Y F , Liu Y , Zheng J J , Tang J , Huang C Z . Chem. Commun., 2011,47:11939. doi: 10.1039/c1cc14294a http://xlink.rsc.org/?DOI=c1cc14294a
[63]	Ding S Y , Dong M , Wang Y W , Chen Y T , Wang H Z , Su C Y , Wang W . J. Am. Chem. Soc., 2016,138:3031. doi: 10.1021/jacs.5b10754 https://www.ncbi.nlm.nih.gov/pubmed/26878337 pmid: 26878337
[64]	Xiong Y H , Qin Y M , Su L J , Ye F G . Chem. Eur. J., 2017,23:11037. doi: 10.1002/chem.201701513 https://www.ncbi.nlm.nih.gov/pubmed/28516466 pmid: 28516466
[65]	Xiong Y H , Su L J , He X G , Duan Z H , Zhang Z , Chen Z L , Xie W , Zhu D J , Luo Y H . Sensor. Actuat. B-Chem., 2017,253:384. doi: 10.1016/j.snb.2017.06.167 https://linkinghub.elsevier.com/retrieve/pii/S0925400517311863
[66]	Zhang Y F , Li R , Xue Q W , Li H B , Liu J F . Microchimi. Acta, 2015,182:1677.
[67]	Sadollahkhani A , Hatamie A , Nur O , Willander M , Zargar B , Kazeminezhad I . ACS Appl. Mater. Interfaces., 2014,6:17694. doi: 10.1021/am505480y https://www.ncbi.nlm.nih.gov/pubmed/25275616 pmid: 25275616
[68]	Pan N , Zhu Y , Wu L , Xie Z , Xue F , Peng C . Anal. Methods., 2016,8:7531. doi: 10.1039/C6AY01789D http://xlink.rsc.org/?DOI=C6AY01789D
[69]	Khalil M M H , Shahat A , Radwan A , El-Shahat M F . Sensor. Actuat. B-Chem., 2016,233:272. doi: 10.1016/j.snb.2016.04.079 https://linkinghub.elsevier.com/retrieve/pii/S0925400516305615
[70]	Li J , Ji C , Hou C , Huo D , Zhang S , Luo X , Yang M , Fa H , Deng B . Sensor. Actuat. B-Chem., 2016,223:853. doi: 10.1016/j.snb.2015.10.017 https://linkinghub.elsevier.com/retrieve/pii/S0925400515304822
[71]	Ma X H , Li S H , Pang C H , Xiong Y H , Li J P . Microchim. Acta., 2018,185:546.
[72]	Cui W R , Zhang C R , Jiang W , Liang R P , Wen S H , Peng D , Qiu J D . ACS Sustainable Chem. Eng., 2019,7:9408.

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Covalent Organic Frameworks(COFs) Materials in Enzyme Immobilization and Mimic Enzymes

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Covalent Organic Frameworks(COFs) Materials in Enzyme Immobilization and Mimic Enzymes