分子模拟辅助设计L-苯丙氨酸分子印迹聚合物及其性能研究
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摘要
对L-苯丙氨酸(L-Phe)为模板分子、分别以氯化1-羧甲基-3-乙烯基咪唑鎓([VIM]Cl)、甲基丙烯酸(MAA)和4-乙烯基吡啶(4-VP)为功能单体,二甲基丙烯酸乙二醇酯(EGDMA)为交联剂的分子印迹组装体系进行分子模拟分析、荧光光谱分析,预测较优功能单体,辅助设计了L-苯丙氨酸分子印迹聚合物(L-MIPs);其次,通过实验系统研究了功能单体种类对L-MIPs的吸附性能和印迹因子的影响,并比较了分别以[VIM]Cl、MAA和4-VP为功能单体制备的L-MIPs的吸附行为,运用多种表征方法对L-MIPs形貌、表面元素组成、热稳定性进行了研究。结果表明,以[VIM]Cl为最优功能单体,且制备的聚合物在300℃内具有较好的热稳定性,在浓度为1. 0mg/m L时,饱和吸附量可达33mg/g,印迹因子可达3. 86。相对于结构类似物D-Phe、L-His或L-Trp,识别因子β分别达到1. 24,1. 41和1. 30。因此,采用计算机模拟的方法对于分子印迹体系的功能单体的筛选及MIPs性能的预测有重要的意义。
In this paper,the molecularly imprinted assembly system of L-phenylalanine(L-Phe) as template molecule,1-vinyl-3-carboxymethylimidazolium chloride([VIM]Cl),methacrylic acid(MAA) or 4-vinyl pyridine(4-VP) as functional monomer,ethylene glycol dimethacrylate EGDMA) as cross-linking agent was analyzed via Gaussian 09 calculation software and fluorescence spectroscopy to predict a proper functional monomer,aiming to prepare L-phenylalanine-imprinted polymers(L-MIPs).The effects of functional monomers on the adsorption performance and imprinting factor of L-MIPs were studied through the experimental system,and the adsorption behaviors of L-MIP prepared with [VIM]Cl,MAA and 4-VP as functional monomers were compared finally.In addition,the morphology,surface element composition and thermal stability of L-MIP were studied by multiple characterization methods.When using [VIM]Cl as monomer,the obtained L-MIP exhibited the best imprinting effect and had good thermal stability within 300℃.The maximum imprinting factor(α) of the obtained L-MIPs could reach 3.86 and the maximum adsorption capacity of L-MIPs for L-Phe was 33.08 mg/g.Compared with the structural analogues of D-Phe,L-His and L-Trp,the recognition factor(β) were 1.24,1.41 and 1.30 respectively.Therefore,it has important significance for selecting proper functional monomer in molecular imprinting system and predicting the performance of MIP through computer simulation.
In this paper,the molecularly imprinted assembly system of L-phenylalanine(L-Phe) as template molecule,1-vinyl-3-carboxymethylimidazolium chloride([VIM]Cl),methacrylic acid(MAA) or 4-vinyl pyridine(4-VP) as functional monomer,ethylene glycol dimethacrylate EGDMA) as cross-linking agent was analyzed via Gaussian 09 calculation software and fluorescence spectroscopy to predict a proper functional monomer,aiming to prepare L-phenylalanine-imprinted polymers(L-MIPs).The effects of functional monomers on the adsorption performance and imprinting factor of L-MIPs were studied through the experimental system,and the adsorption behaviors of L-MIP prepared with [VIM]Cl,MAA and 4-VP as functional monomers were compared finally.In addition,the morphology,surface element composition and thermal stability of L-MIP were studied by multiple characterization methods.When using [VIM]Cl as monomer,the obtained L-MIP exhibited the best imprinting effect and had good thermal stability within 300℃.The maximum imprinting factor(α) of the obtained L-MIPs could reach 3.86 and the maximum adsorption capacity of L-MIPs for L-Phe was 33.08 mg/g.Compared with the structural analogues of D-Phe,L-His and L-Trp,the recognition factor(β) were 1.24,1.41 and 1.30 respectively.Therefore,it has important significance for selecting proper functional monomer in molecular imprinting system and predicting the performance of MIP through computer simulation.
引文
[1]徐伟箭,刘玉堂,项伟中等.湖南大学学报(自然科学版),2004,31(4):1~5.
[2]J Matsui,I Nicholls,I Karube et al.J.Org.Chem.,1996,61:5414~5417.
[3]V Abbate,A R Bassindale,K F Brandstadt et al.J.Catal.,2011,284:68~76.
[4]Y Hoshino,H Koide,T Urakami.J.Am.Chem.Soc.,2010,132:6644~6645.
[5]J Yin,G Yang,Y Chen.J.Chromatogr.A,2005,1090(1):68~75.
[6]B Y Huang,Y C Chen,G R Wang et al.J.Chromatogr.A,2011,1218(6):849~855.
[7]R Wang,Y Wang,C Xue et al.J.Sep.Sci.,2013,36:1015~1021.
[8]R Levi,S Mc Niven,S Piletsky et al.Anal.Chem.,1997,69(11):2017~2021.
[9]P Andrea,S Miroslav,S Silvia et al.Sens.Actuat.B,2001,76(1):286~294.
[10]S M Reddy,Q T Phan,H El-Sharif et al.Biomacromolecules,2012,13:3959~3965.
[11]L I Andersson.Analyst,2000,125(9):1515~1517.
[12]H F Wang,Y Z Zhu,X P Yan et al.Adv.Mater.,2006,18(24):3266~3270.
[13]J P Fan,Z Y Tian,S Tong et al.Food Chem.,2013,141(4):3578~3585.
[14]Q Li,Q Y Yue,Y Su et al.J.Chem.Eng.,2010,158(3):489~497.
[15]李思平,徐伟箭.合成化学,2009,17(2):187~191.
[16]L Wu,Y Li.J.Mol.Recognit.,2004,17(6):567~574.
[17]H Y Lin,C Y Hsu,J L Thomas et al.Biosens.Bioelectron.,2006,22:534~543.
[18]X Luo,R Dong,S Luo et al.J.Appl.Polym.Sci.,2013,127(4):2884~2890.
[19]G Bo,G Ping,H Xiaoling et al.Des.Monomers Polym.,2015,18(3):185~198.
[20]L Qian,X Hu,P Guan et al.Talanta,2014,121:56~64.
[2]J Matsui,I Nicholls,I Karube et al.J.Org.Chem.,1996,61:5414~5417.
[3]V Abbate,A R Bassindale,K F Brandstadt et al.J.Catal.,2011,284:68~76.
[4]Y Hoshino,H Koide,T Urakami.J.Am.Chem.Soc.,2010,132:6644~6645.
[5]J Yin,G Yang,Y Chen.J.Chromatogr.A,2005,1090(1):68~75.
[6]B Y Huang,Y C Chen,G R Wang et al.J.Chromatogr.A,2011,1218(6):849~855.
[7]R Wang,Y Wang,C Xue et al.J.Sep.Sci.,2013,36:1015~1021.
[8]R Levi,S Mc Niven,S Piletsky et al.Anal.Chem.,1997,69(11):2017~2021.
[9]P Andrea,S Miroslav,S Silvia et al.Sens.Actuat.B,2001,76(1):286~294.
[10]S M Reddy,Q T Phan,H El-Sharif et al.Biomacromolecules,2012,13:3959~3965.
[11]L I Andersson.Analyst,2000,125(9):1515~1517.
[12]H F Wang,Y Z Zhu,X P Yan et al.Adv.Mater.,2006,18(24):3266~3270.
[13]J P Fan,Z Y Tian,S Tong et al.Food Chem.,2013,141(4):3578~3585.
[14]Q Li,Q Y Yue,Y Su et al.J.Chem.Eng.,2010,158(3):489~497.
[15]李思平,徐伟箭.合成化学,2009,17(2):187~191.
[16]L Wu,Y Li.J.Mol.Recognit.,2004,17(6):567~574.
[17]H Y Lin,C Y Hsu,J L Thomas et al.Biosens.Bioelectron.,2006,22:534~543.
[18]X Luo,R Dong,S Luo et al.J.Appl.Polym.Sci.,2013,127(4):2884~2890.
[19]G Bo,G Ping,H Xiaoling et al.Des.Monomers Polym.,2015,18(3):185~198.
[20]L Qian,X Hu,P Guan et al.Talanta,2014,121:56~64.