花椒麻味物质分子印迹预组装体系的分子模拟与吸附性能
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摘要
为制备花椒麻味物质的分子印迹聚合物(MIPs)和解决花椒麻味物质难以洗脱的困难,以作者合成的花椒麻味类似物为模板分子,以Gaussian 03W中的MNDO-PM3(Parametric Method 3,PM3)法优化花椒麻味类似物及功能单体的分子结构,得出花椒麻味类似物、功能单体及花椒麻味类似物-功能单体结合物的最低能量构象图、单点能和Mulliken电荷,并筛选出最佳功能单体为甲基亚氨基二乙酸。结合实际情况确定花椒麻味类似物与功能单体的物质的量比为1∶4。在此基础上,采用Hartree-Fock方法,运用6-31G+(d)基组选取极化连续溶剂模型(PCM),以溶剂化能筛选出最佳致孔剂为乙腈。为了验证计算机分子模拟技术的准确性,选择3种功能单体及3种致孔剂制备相应的分子印迹聚合物,评价它们的动态吸附与静态吸附能力。试验证实计算机分子模拟技术在花椒麻味物质分子印迹预组装体系中的实用性,为快速制备分子印迹聚合物提供理论支持。
For preparing the molecular imprinted polymer of numb-taste components, the molecular structure of numb-taste components analogues and functional monomers were optimized by Gaussian 03 W MNDO-PM3(Parametric Method 3, PM3) method, and then obtained the lowest energy conformation diagram, single point energy and Mulliken charge, finally elected the best functional monomer was N-Methyliminodiacetic acid and the molar ratio of the numb-taste components and functional monomer was 1 ∶ 4. On this basis, electing the pore-foaming agent by using Hartree-Fock method which the basis set is 6-31 G +(d) in polarization continuum solvent model. In order to verify the accuracy of simulation technology of computer molecular, three kinds of functional monomer and three kinds of pore-foaming agent were selected to prepare molecular imprinted poly-mers, and then assesse their dynamic adsorption capacity and static adsorption capacity, the results proving that the computer molecular simulation technology is useful for the application of t the molecular imprinted polymer of numb-taste components, which provides theoretical support for the preparation of numb taste components MIPs.
For preparing the molecular imprinted polymer of numb-taste components, the molecular structure of numb-taste components analogues and functional monomers were optimized by Gaussian 03 W MNDO-PM3(Parametric Method 3, PM3) method, and then obtained the lowest energy conformation diagram, single point energy and Mulliken charge, finally elected the best functional monomer was N-Methyliminodiacetic acid and the molar ratio of the numb-taste components and functional monomer was 1 ∶ 4. On this basis, electing the pore-foaming agent by using Hartree-Fock method which the basis set is 6-31 G +(d) in polarization continuum solvent model. In order to verify the accuracy of simulation technology of computer molecular, three kinds of functional monomer and three kinds of pore-foaming agent were selected to prepare molecular imprinted poly-mers, and then assesse their dynamic adsorption capacity and static adsorption capacity, the results proving that the computer molecular simulation technology is useful for the application of t the molecular imprinted polymer of numb-taste components, which provides theoretical support for the preparation of numb taste components MIPs.
引文
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[9]尚宏周,梁红玉,张小梅,等.分子印迹聚合物的最新研究进展[J].现代化工,2013,33(12):28-32.
[10]丛姣姣,罗静,高雅涵,等.表面分子印迹研究进展[J].高分子通报,2015,(5):10-20.
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[18]WU L Q,ZHU K C,ZHAO M P,at al.Theoretical and experimental study of nicotinamide molecularly imprinted polymers with different porogena[J].Analytica Chimica Acta,2005,549(2):39-44.
[19]YOSHIKI K W,CHIKASHI 1,HITOSHI K,et al.Amides of the fruit of Zanthoxylum,SPP[J].Phytochemistry,1997,44(6):1125-1127.
[20]E.邦巴德里,B.盖贝塔.花椒的提取物,含有它们的药物和化妆品制剂:CN1308541A[P].2001-08-15.
[21]NAVARRETE A.Anthelmintic properties ofα-anshool from Zanthoxylum libmannianum[J].Planta Med,1996,62(3):250-251.
[22]HASHIMOTO,SATO K,KASE K Y,et al.Modulatory effect of aliphatic acid amides from Zanthoxylum piperitum onisolated gastrointestinal tract[J].Planta Medica,2001,67(2):179-181.
[23]曹继全,徐伟昌,李春荣.高温高压水煮制取花椒麻味素的方法:CN1305742A[P].2001-08.
[24]刘雄.花椒风味物质的提取与分离技术的研究[D].重庆:西南农业大学,2003.
[25]CHEN I S,CHEN T L,LIN W Y,et al.Isobutyl amides from the fruit of Zanthoxylum integrifoliolum[J].Phytochemistry,1999,52:357-360.
[26]XIONG Q B,SHI D W,HIROFUMI,et al.Alkyl amides from Pericarps of Zanthoxylum[J].Phytochemistry,1997,46(6):1123-1126.
[27]孙晓明,金敬宏,张卫明,等.利用超临界流体技术分离花椒麻味成分的工艺:CN 1488289A[P].2004-04-14.
[28]刘雄,阚建全,付陈梅,等.花椒麻昧成分的提取与分离技术[J].食品与发酵工业,2004,30(9):113-115.
[29]杨文明.表面分子印迹聚合物的制备与性能研究及计算机辅助设计[D].镇江:江苏大学,2013.
[30]李文静,胡艳云,韩芳等.三唑酮分子印迹预组装体系的分子模拟与吸附性能[J].高等学校化学学报,2013,34(5):1219-1225.
[31]刘路宽,杨文明,徐婉珍,等.分子模拟辅助设计磁敏型分子印迹聚合物的制备及性能研究[J].分析化学,2014,42(2):249-257.
[32]李萍,戎非,朱馨乐,等.以右旋邻氯扁桃酸(L-2-MDA)为模板分子印迹聚合物的研究[J].高分子学报,2003,(5):724-728.
[33]李萍,胡哲,林保平,等.以混旋邻氯扁桃酸为模板的分子印迹聚合物的制备及拆分性能研究[J].化学学报.2003,61(11):1885-1889.
[34]陈志萍,高保娇,杨晓峰,等.表面印迹法制备胆红素分子印迹材料及其识别性能[J].过程工程学报,2009,9(2):387-392.
[35]沈金灿,吴凤琪,肖陈贵,等.硅胶表面水胺硫磷分子印迹聚合物的制备及其性能[J].应用化学,2014,31(1):84-88.
[36]杨律文,刘含茂,屈贺幂,等.硅胶表面熊果酸分子印迹聚合物的制备和分子识别特性[J].应用化学,2008,2:137-141.
[37]陈颜婷.硅胶表面苏丹红1分子印迹聚合物的制备与性能考察[J].化学研究与应用,2015,27(12):1875-1878.
[38]张腊梅,李道敏,李兆周,等.乙氧酰胺苯甲酯表面分子印迹聚合物的制备与吸附特性[J].食品科学,2016,37(4):226-232.
[39]宁左云.计算机分子模拟研究磺胺类药物分子印迹体系[D].衡阳:南华大学,2012.
[40]韩瑞芳.用双重识别基团分子印迹聚合物富集天然微量蛋白质的研究[D].天津:南开大学,2009.
[2]MOSBACH K,RAMSTROM O.Emerging technique of molecular imprinting and its future impact on biotechnology[J].Bio/Technology,1996,14(2):163-172.
[3]ANDREW G,MAYES,KLAUS M.Molecularly imprinted polymers:useful materials for analytical chemistry[J].Trends in Analytical Chemistry,1997,16(6):321-333.
[4]LIU J F,CHAO J B,JIANG G B,et al.Trace analysis of sulfonylurea herbicides in water by online continuous flow liquid membrane extraction C18precolumn liquid chromatoraphy with ultraviolet absorbance detection[J].Journal of Chromatography A,2003,995(1):21-28.
[5]LARS I A.Molecular imprinting:developments and applications in the analytical chemistryfield[J].Journal of Chromatography B,2000,745(1):3-13.
[6]SREENIVASAN K.Surface imprinted polyurethane film as a chiral discriminator[J].Talanta,2006,68(3):1037-1039.
[7]BALJIT S,NIRMALA C.Preliminary evaluation of molecular imprinting of 5-fluorouracil within hydrogels for use as drug delivery systems[J].Acta Biomaterialia,2008,4(5):1244-1254.
[8]CHRYSA M,PANAGIOTIS M,COSTAS P.Synthesis of caffeic acid and phydroxybenzoic acid molecularly imprinted polymers and their application for the selective extraction of polyphenols from olive mill waste waters[J].Journal of Chromatography A,2008,1182(1):25-33.
[9]尚宏周,梁红玉,张小梅,等.分子印迹聚合物的最新研究进展[J].现代化工,2013,33(12):28-32.
[10]丛姣姣,罗静,高雅涵,等.表面分子印迹研究进展[J].高分子通报,2015,(5):10-20.
[11]VILLAR P,WHITCOMBE M J,VULFSON E N.Mateix effects on the selectivity of acholesterol-im printed polymer[J].Polymer,2007,48(6):1483-1489.
[12]刘英,王芳,谭天伟.分子模拟在分子印迹技术中的应用[J].化工学报,2006,57(10):2257-2262.
[13]WULFF G,GROSS T,SCHONFELD R,et al.Molecular imprinting for the preparation of enzymeanalogous polymers.[J].Acs Symposium,1998,703:10-28.
[14]PAVEL D,LAGOWSKI J.Computationally designed monomers and polymers for molecular imprinting of theophylline-part I[J].Polymer,2005,46(18):7528-7542.
[15]PAVEL D,LAGOWSKI J.Computationally designed monomers and polymers for molecular imprinting of theophylline-part II[J].Polymer,2005,46(18):7543-7556.
[16]PAVEL D,LAGOWSKI J,LEPAGE C J.Computationally Designed monomers for molecular imprinting of vhemical warfare agents-part V[J].Polymer,2006,47(25):8389-8399.
[17]DONG W G,YAN M,ZHANG M L,at al.Effect of functional monomer on molecular recognition of molecularly imprinted polymer:quantum chemical calculation and experimental investigation[J].Journal of Chemical Industry and Engineering(China),2004,62(6):598-602.
[18]WU L Q,ZHU K C,ZHAO M P,at al.Theoretical and experimental study of nicotinamide molecularly imprinted polymers with different porogena[J].Analytica Chimica Acta,2005,549(2):39-44.
[19]YOSHIKI K W,CHIKASHI 1,HITOSHI K,et al.Amides of the fruit of Zanthoxylum,SPP[J].Phytochemistry,1997,44(6):1125-1127.
[20]E.邦巴德里,B.盖贝塔.花椒的提取物,含有它们的药物和化妆品制剂:CN1308541A[P].2001-08-15.
[21]NAVARRETE A.Anthelmintic properties ofα-anshool from Zanthoxylum libmannianum[J].Planta Med,1996,62(3):250-251.
[22]HASHIMOTO,SATO K,KASE K Y,et al.Modulatory effect of aliphatic acid amides from Zanthoxylum piperitum onisolated gastrointestinal tract[J].Planta Medica,2001,67(2):179-181.
[23]曹继全,徐伟昌,李春荣.高温高压水煮制取花椒麻味素的方法:CN1305742A[P].2001-08.
[24]刘雄.花椒风味物质的提取与分离技术的研究[D].重庆:西南农业大学,2003.
[25]CHEN I S,CHEN T L,LIN W Y,et al.Isobutyl amides from the fruit of Zanthoxylum integrifoliolum[J].Phytochemistry,1999,52:357-360.
[26]XIONG Q B,SHI D W,HIROFUMI,et al.Alkyl amides from Pericarps of Zanthoxylum[J].Phytochemistry,1997,46(6):1123-1126.
[27]孙晓明,金敬宏,张卫明,等.利用超临界流体技术分离花椒麻味成分的工艺:CN 1488289A[P].2004-04-14.
[28]刘雄,阚建全,付陈梅,等.花椒麻昧成分的提取与分离技术[J].食品与发酵工业,2004,30(9):113-115.
[29]杨文明.表面分子印迹聚合物的制备与性能研究及计算机辅助设计[D].镇江:江苏大学,2013.
[30]李文静,胡艳云,韩芳等.三唑酮分子印迹预组装体系的分子模拟与吸附性能[J].高等学校化学学报,2013,34(5):1219-1225.
[31]刘路宽,杨文明,徐婉珍,等.分子模拟辅助设计磁敏型分子印迹聚合物的制备及性能研究[J].分析化学,2014,42(2):249-257.
[32]李萍,戎非,朱馨乐,等.以右旋邻氯扁桃酸(L-2-MDA)为模板分子印迹聚合物的研究[J].高分子学报,2003,(5):724-728.
[33]李萍,胡哲,林保平,等.以混旋邻氯扁桃酸为模板的分子印迹聚合物的制备及拆分性能研究[J].化学学报.2003,61(11):1885-1889.
[34]陈志萍,高保娇,杨晓峰,等.表面印迹法制备胆红素分子印迹材料及其识别性能[J].过程工程学报,2009,9(2):387-392.
[35]沈金灿,吴凤琪,肖陈贵,等.硅胶表面水胺硫磷分子印迹聚合物的制备及其性能[J].应用化学,2014,31(1):84-88.
[36]杨律文,刘含茂,屈贺幂,等.硅胶表面熊果酸分子印迹聚合物的制备和分子识别特性[J].应用化学,2008,2:137-141.
[37]陈颜婷.硅胶表面苏丹红1分子印迹聚合物的制备与性能考察[J].化学研究与应用,2015,27(12):1875-1878.
[38]张腊梅,李道敏,李兆周,等.乙氧酰胺苯甲酯表面分子印迹聚合物的制备与吸附特性[J].食品科学,2016,37(4):226-232.
[39]宁左云.计算机分子模拟研究磺胺类药物分子印迹体系[D].衡阳:南华大学,2012.
[40]韩瑞芳.用双重识别基团分子印迹聚合物富集天然微量蛋白质的研究[D].天津:南开大学,2009.
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