CIESC Journal ›› 2019, Vol. 70 ›› Issue (6): 2221-2228.DOI: 10.11949/j.issn.0438-1157.20190074
• Biochemical engineering and technology • Previous Articles Next Articles
Chao XU(),Yu XUE,Hongyue CHEN,Yi HU()
Received:
2019-01-25
Revised:
2019-03-22
Online:
2019-06-05
Published:
2019-06-05
Contact:
Yi HU
通讯作者:
胡燚
作者简介:
<named-content content-type="corresp-name">徐超</named-content>(1994—),男,硕士研究生,<email>XCsuper@foxmail.com</email>
基金资助:
CLC Number:
Chao XU, Yu XUE, Hongyue CHEN, Yi HU. Study on catalytic properties of porcine pancreatic lipase modified by chiral proline ionic liquids[J]. CIESC Journal, 2019, 70(6): 2221-2228.
徐超, 薛誉, 陈虹月, 胡燚. 手性脯氨酸类离子液体化学修饰猪胰脂肪酶催化性能研究[J]. 化工学报, 2019, 70(6): 2221-2228.
酶 | 修饰剂 | 修饰度①/% | 酶活②/ (U/mg) | 相对 酶活/% |
---|---|---|---|---|
PPL-0 | 8.58 | 100 | ||
PPL-1 | [BMIM][N-AC-D-Pro] | 20.0 | 8.06 | 93.94 |
PPL-2 | [BMIM][N-AC-L-Pro] | 22.4 | 17.29 | 201.52 |
PPL-3 | [N-AC-D-Pro][Cl] | 23.3 | 18.23 | 212.47 |
PPL-4 | [N-AC-L-Pro][Cl] | 26.6 | 21.56 | 251.28 |
Table 1 Modification degree and initial enzyme activity
酶 | 修饰剂 | 修饰度①/% | 酶活②/ (U/mg) | 相对 酶活/% |
---|---|---|---|---|
PPL-0 | 8.58 | 100 | ||
PPL-1 | [BMIM][N-AC-D-Pro] | 20.0 | 8.06 | 93.94 |
PPL-2 | [BMIM][N-AC-L-Pro] | 22.4 | 17.29 | 201.52 |
PPL-3 | [N-AC-D-Pro][Cl] | 23.3 | 18.23 | 212.47 |
PPL-4 | [N-AC-L-Pro][Cl] | 26.6 | 21.56 | 251.28 |
Enzyme | C 总 | CR | CS | eeS | eeR | E |
---|---|---|---|---|---|---|
PPL-0 | 29.5 | 49.1 | 15.8 | 24.1 | 62.1 | 5.5 |
PPL-1 | 56.3 | 39.5 | 11.2 | 23.5 | 59.5 | 8.8 |
PPL-2 | 62.2 | 44.8 | 12.5 | 30.5 | 58.3 | 13.9 |
PPL-3 | 36.3 | 52.8 | 14.0 | 25.4 | 63.3 | 6.3 |
PPL-4 | 43.2 | 54.6 | 13.4 | 26.1 | 64.2 | 7.4 |
Table 2 Enantioselectivity parameters in transesterification of α -phenyl ethanol
Enzyme | C 总 | CR | CS | eeS | eeR | E |
---|---|---|---|---|---|---|
PPL-0 | 29.5 | 49.1 | 15.8 | 24.1 | 62.1 | 5.5 |
PPL-1 | 56.3 | 39.5 | 11.2 | 23.5 | 59.5 | 8.8 |
PPL-2 | 62.2 | 44.8 | 12.5 | 30.5 | 58.3 | 13.9 |
PPL-3 | 36.3 | 52.8 | 14.0 | 25.4 | 63.3 | 6.3 |
PPL-4 | 43.2 | 54.6 | 13.4 | 26.1 | 64.2 | 7.4 |
Sample | Alpha helix/% | Total beta-sheet/% | Beta-turn/% | Random coil/% |
---|---|---|---|---|
PPL-0 | 22.9 | 27.5 | 17.8 | 31.5 |
PPL-1 | 14.5 | 35.8 | 16.5 | 33.2 |
PPL-2 | 17.1 | 33.2 | 16.1 | 32.6 |
PPL-3 | 19.3 | 30.2 | 16.9 | 32.6 |
PPL-4 | 20.6 | 32.3 | 16.8 | 30.3 |
Table 3 Percentage of secondary structures of native PPL and modified PPLs
Sample | Alpha helix/% | Total beta-sheet/% | Beta-turn/% | Random coil/% |
---|---|---|---|---|
PPL-0 | 22.9 | 27.5 | 17.8 | 31.5 |
PPL-1 | 14.5 | 35.8 | 16.5 | 33.2 |
PPL-2 | 17.1 | 33.2 | 16.1 | 32.6 |
PPL-3 | 19.3 | 30.2 | 16.9 | 32.6 |
PPL-4 | 20.6 | 32.3 | 16.8 | 30.3 |
1 | Egorova K S , Gordeev E G , Ananikov V P . Biological activity of ionic liquids and their application in pharmaceutics and medicine[J]. Chem. Rev., 2017, 117(10): 7132-7189. |
2 | Vekariya R L . A review of ionic liquids: applications towards catalytic organic transformations[J]. J. Mol. Liq., 2017, 227: 44-60. |
3 | Itoh T . Ionic liquids as tool to improve enzymatic organic synthesis[J]. Chem. Rev., 2017, 117(15): 10567-10607. |
4 | 李明, 方银军, 李在均, 等 . 新型对称烷基咪唑离子液体介质中酶催化合成l-乙酸薄荷酯[J]. 化学学报, 2009, 67(11): 1252-1258. |
Li M , Fang Y J , Li Z J . et al . Synthesis of l-menthyl acetate catalyzed by lipase in new symmetrical 1, 3-dialkylimidazolium ionic liquids[J]. Acta Chim. Sinica, 2009, 67(11): 1252-1258. | |
5 | Tao G H , He L , Sun N , et al . New generation ionic liquids: cations derived from amino acids[J]. Chem. Commun. (Cambridge, U K), 2005, 28(28): 3562-3564. |
6 | 吴阳, 张甜甜, 李静蕊 . 半胱氨酸阴离子与咪唑阳离子间相互作用的理论研究[J]. 化学学报, 2009, 67(16): 1851-1858. |
Wu Y , Zhang T T , Li J R . A theoretical investigation of interaction between 1-ethyl-3-methylimidazolium cation and cysteine anion[J]. Acta Chim. Sinica, 2009, 67(16): 1851-1858. | |
7 | Mu X Y , Qi L , Zhang H Z , et al . Ionic liquids with amino acids as cations: novel chiral ligands in chiral ligand-exchange capillary electrophoresis[J]. Talanta, 2012, 97: 349-354. |
8 | Pereira M P , de Souza Martins R , de Oliveira M A L , et al . Amino acid ionic liquids as catalysts in a solvent-free Morita–Baylis–Hillman reaction[J]. RSC Advances, 2018, 8(42): 23903-23913. |
9 | Wahl J , Holzgrabe U . Capillary electrophoresis separation of phenethylamine enantiomers using amino acid based ionic liquids[J]. J. Pharm. Biomed. Anal. , 2018, 148: 245-250. |
10 | Liu W , Zhu X S . Simultaneous determination of Magnolol and Honokiol by amino acid ionic liquid synchronous fluorescence spectrometry[J]. Spectrochim Acta, Part A, 2018, 196: 141-147. |
11 | Gathergood N , Garcia M T , Scammells P J . Biodegradable ionic liquids (Part I): Concept, preliminary targets and evaluation[J]. Green Chem. , 2004, 6(3): 166-175. |
12 | Docherty K M , Kulpa J C F . Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids[J]. Green Chem. , 2005, 7(4): 185-189. |
13 | Fukumoto K , Ohno H . Design and synthesis of hydrophobic and chiral anions from amino acids as precursor for functional ionic liquids[J]. Chemical Communications, 2006, (29): 3081-3083. |
14 | Chado G R , Holland E N , Tice A K , et al . Modification of lipase with poly(4-acryloylmorpholine) enhances solubility and transesterification activity in anhydrous ionic liquids[J]. Biomacromolecules, 2018, 19(4): 1324-1332. |
15 | Ueji S , Ueda A , Tanaka H , et al . Chemical modification of lipases with various hydrophobic groups improves their enantioselectivity in hydrolytic reactions[J]. Biotechnol. Lett. , 2003, 25(1): 83-87. |
16 | Zhao H , Song Z Y . Nuclear magnetic relaxation of water in ionic-liquid solutions: determining the kosmotropicity of ionic liquids and its relationship with the enzyme enantioselectivity[J]. Journal of Chemical Technology & Biotechnology, 2007, 82(3): 304-312. |
17 | Evran S , Telefoncu A . Modification of porcine pancreatic lipase with Z-proline[J]. Prep. Biochem. Biotechnol. , 2005, 35(3): 191-201. |
18 | Nwagu T N , Okolo B , Aoyagi H , et al . Chemical modification with phthalic anhydride and chitosan: viable options for the stabilization of raw starch digesting amylase from Aspergillus carbonarius [J]. Int. J. Biol. Macromol., 2017, 99: 641-647. |
19 | Li C , Huang Z L , Dong L , et al . Improvement of enzymological properties of pepsin by chemical modification with chitooligosaccharides[J]. Int. J. Biol. Macromol., 2018, 118: 216-227. |
20 | Xu C , Yin X H , Zhang C , et al . Improving catalytic performance of burkholderiacepacia lipase by chemical modification with functional ionic liquids[J]. Chem. Res. Chin. Univ., 2018, 34(2): 279-284. |
21 | Jia R , Hu Y , Liu L , et al . Enhancing catalytic performance of porcine pancreatic lipase by covalent modification using functional ionic liquids[J]. ACS Catal., 2013, 3(9): 1976-1983. |
22 | Li X J , Zhang C , Li S , et al . Improving catalytic performance of Candida rugosa lipase by chemical modification with polyethylene glycol functional ionic liquids[J]. Ind. Eng. Chem. Res. , 2015, 54(33): 8072-8079. |
23 | 熊亚红, 苏健鸿, 刘小平 . 邻苯二甲酸酐修饰脂肪酶的性能研究[J]. 华南农业大学学报, 2011, 32(2): 122. |
Xiong Y X , Su J H , Liu X P . Study on the property of pocine pancreas lipase modified with phthalic anhydride[J]. Journal of South China Agricultural University, 2011, 32(2): 122. | |
24 | 张川, 张鲁嘉, 张洋, 等 . 基于分子模拟的离子液体修饰 Porcine Pancreas 脂肪酶催化性能和稳定性的相关研究[J]. 化学学报, 2016, 74: 74-80, |
Zhang C , Zhang L J , Zhang Y , et al . Study on the stability and enzymatic property improvement of porcine pancreas lipase modified by ionic liquids using molecular simulation[J]. Acta Chim. Sinica, 2016, 74: 74-80. | |
25 | Zhao H . Are ionic liquids kosmotropic or chaotropic? An evaluation of available thermodynamic parameters for quantifying the ion kosmotropicity of ionic liquids[J]. Journal of Chemical Technology & Biotechnology, 2006, 81(6): 877-891. |
26 | Silman I H , Weissenberg M A , Katchalski E . Some water-insoluble papain derivatives[J]. Biopolymers, 1966, 4(4): 441-448. |
27 | Sangeetha K , Abraham T E . Chemical modification of papain for use in alkaline medium [J]. Journal of Molecular Catalysis B: Enzymatic, 2006, 38: 171-177. |
28 | 张静, 田亚平 . 丁二酸酐修饰对枯草芽孢杆菌氨肽酶结构及酶学特性的影响 [J]. 食品与生物技术学报, 2013, 32(6): 622-627. |
Zhang J , Tian Y P . Chemical modification of the Bacillus subtilis aminopeptidase by succinic anhydride and its enzyme properties [J]. Journal of Food Science and Biotechnology, 2013, 32(6): 622-627. | |
29 | 贺俊斌, 林日辉, 龙寒, 等 . 乙二胺四乙酸二酐对草酸脱羧酶的修饰改性[J]. 化工学报, 2016, 67(10): 4389-4398. |
He J B , Lin R H , Long H , et al . Chemical modification of oxalate decarboxylase with ethylenediaminetetraacetic dianhydride[J]. CIESC Journal, 2016, 67(10): 4389-4398. | |
30 | Grochulski P , Li Y , Schrag J D , et al . Insights into interfacial activation from an open structure of candida rugosa lipase[J]. J. Biol. Chem. , 1993, 268(17): 12843-12847. |
31 | Hu Y , Yang J , Jia R , et al . Chemical modification with functionalized ionic liquids: a novel method to improve the enzymatic properties of Candida rugosa lipase[J]. Bioprocess Biosyst. Eng. , 2014, 37(8): 1617-1626. |
32 | Ladokhin A S , Jayasinghe S , White S H . How to measure and analyze tryptophan fluorescence in membranes properly, and why bother?[J]. Anal. Biochem. , 2000, 285(2): 235-245. |
33 | Lozano P , De Diego T , Iborra J L . Dynamic structure/function relationships in the alpha-chymotrypsin deactivation process by heat and pH[J]. Eur.J. Biochem. , 1997, 248(1): 80-85. |
34 | Shokri M M , Ahmadian S , Akbari N , et al . Hydrophobic substitution of surface residues affects lipase stability in organic solvents[J]. Mol. Biotechnol. , 2014, 56: 360-368. |
35 | Rahman R N Z A , Tejo B A , Basri M , et al . Reductive alkylation of lipase - experimental and molecular modeling approaches[J]. Appl. Biochem. Biotechnol. , 2004, 118: 11-20. |
[1] | Qi WANG, Bin ZHANG, Xiaoxin ZHANG, Hujian WU, Haitao ZHAN, Tao WANG. Synthesis of isoxepac and 2-ethylanthraquinone catalyzed by chloroaluminate-triethylamine ionic liquid/P2O5 [J]. CIESC Journal, 2023, 74(S1): 245-249. |
[2] | Ruimin CHE, Wenqiu ZHENG, Xiaoyu WANG, Xin LI, Feng XU. Research progress on homogeneous processing of cellulose in ionic liquids [J]. CIESC Journal, 2023, 74(9): 3615-3627. |
[3] | Minghao SONG, Fei ZHAO, Shuqing LIU, Guoxuan LI, Sheng YANG, Zhigang LEI. Multi-scale simulation and study of volatile phenols removal from simulated oil by ionic liquids [J]. CIESC Journal, 2023, 74(9): 3654-3664. |
[4] | Shaoqi YANG, Shuheng ZHAO, Lungang CHEN, Chenguang WANG, Jianjun HU, Qing ZHOU, Longlong MA. Hydrodeoxygenation of lignin-derived compounds to alkanes in Raney Ni-protic ionic liquid system [J]. CIESC Journal, 2023, 74(9): 3697-3707. |
[5] | Meisi CHEN, Weida CHEN, Xinyao LI, Shangyu LI, Youting WU, Feng ZHANG, Zhibing ZHANG. Advances in silicon-based ionic liquid microparticle enhanced gas capture and conversion [J]. CIESC Journal, 2023, 74(9): 3628-3639. |
[6] | Lizhi WANG, Qiancheng HANG, Yeling ZHENG, Yan DING, Jiaji CHEN, Qing YE, Jinlong LI. Separation of methyl propionate + methanol azeotrope using ionic liquid entrainers [J]. CIESC Journal, 2023, 74(9): 3731-3741. |
[7] | Jie CHEN, Yongsheng LIN, Kai XIAO, Chen YANG, Ting QIU. Study on catalytic synthesis of sec-butanol by tunable choline-based basic ionic liquids [J]. CIESC Journal, 2023, 74(9): 3716-3730. |
[8] | Zehao MI, Er HUA. DFT and COSMO-RS theoretical analysis of SO2 absorption by polyamines type ionic liquids [J]. CIESC Journal, 2023, 74(9): 3681-3696. |
[9] | Lingding MENG, Ruqing CHONG, Feixue SUN, Zihui MENG, Wenfang LIU. Immobilization of carbonic anhydrase on modified polyethylene membrane and silica [J]. CIESC Journal, 2023, 74(8): 3472-3484. |
[10] | Yaxin CHEN, Hang YUAN, Guanzhang LIU, Lei MAO, Chun YANG, Ruifang ZHANG, Guangya ZHANG. Advances in enzyme self-immobilization mediated by protein nanocages [J]. CIESC Journal, 2023, 74(7): 2773-2782. |
[11] | Xiaoling TANG, Jiarui WANG, Xuanye ZHU, Renchao ZHENG. Biosynthesis of chiral epichlorohydrin by halohydrin dehalogenase based on Pickering emulsion system [J]. CIESC Journal, 2023, 74(7): 2926-2934. |
[12] | Yuanliang ZHANG, Xinqi LUAN, Weige SU, Changhao LI, Zhongxing ZHAO, Liqin ZHOU, Jianmin CHEN, Yan HUANG, Zhenxia ZHAO. Study on selective extraction of nicotine by ionic liquids composite extractant and DFT calculation [J]. CIESC Journal, 2023, 74(7): 2947-2956. |
[13] | Lei MAO, Guanzhang LIU, Hang YUAN, Guangya ZHANG. Efficient preparation of carbon anhydrase nanoparticles capable of capturing CO2 and their characteristics [J]. CIESC Journal, 2023, 74(6): 2589-2598. |
[14] | Lanhe ZHANG, Qingyi LAI, Tiezheng WANG, Xiaozhuo GUAN, Mingshuang ZHANG, Xin CHENG, Xiaohui XU, Yanping JIA. Effect of H2O2 on nitrogen removal and sludge properties in SBR [J]. CIESC Journal, 2023, 74(5): 2186-2196. |
[15] | Lufan JIA, Yiying WANG, Yuman DONG, Qinyuan LI, Xin XIE, Hao YUAN, Tao MENG. Aqueous two-phase system based adherent droplet microfluidics for enhanced enzymatic reaction [J]. CIESC Journal, 2023, 74(3): 1239-1246. |
Viewed | ||||||||||||||||||||||||||||||||||||||||||||||||||
Full text 296
|
|
|||||||||||||||||||||||||||||||||||||||||||||||||
Abstract 485
|
|
|||||||||||||||||||||||||||||||||||||||||||||||||