Computational Design and Fabrication of Enantioselective Recognition Sorbents for L-phenylalanine Benzyl Ester on Multiwalled Carbon Nanotubes Using Molecular Imprinting Technology

T Sajini; Renjith Thomas; Beena Mathew

doi:10.1007/s10118-019-2282-4

Your Location：

Home >

Browse articles >

Computational Design and Fabrication of Enantioselective Recognition Sorbents for L-phenylalanine Benzyl Ester on Multiwalled Carbon Nanotubes Using Molecular Imprinting Technology

ARTICLE | Updated：2021-02-18

- Computational Design and Fabrication of Enantioselective Recognition Sorbents for L-phenylalanine Benzyl Ester on Multiwalled Carbon Nanotubes Using Molecular Imprinting Technology
- Computational Design and Fabrication of Enantioselective Recognition Sorbents for L-phenylalanine Benzyl Ester on Multiwalled Carbon Nanotubes Using Molecular Imprinting Technology
- Chinese Journal of Polymer Science 2019年37卷第12期页码：1305-1318
- Affiliations：
  
  a.Research & Post Graduate Department of Chemistry, St. Berchmans College (Autonomous), Affiliated to Mahatma Gandhi University, Changanassery 686101, India
  b.School of Chemical Sciences, Mahatma Gandhi University, Priyadarsini Hills P O, Kottayam 686560, India
- Author bio：
  
  beenamscs@gmail.com
- Funds：
- DOI：10.1007/s10118-019-2282-4
  中图分类号：
- 收稿：2019-03-25，
  
  修回：2019-4-11，
  
  录用：2019-4-22，
  
  网络首发：2019-06-18，
  
  纸质出版：2019-12
- Accepted：
Scan QR Code
Sajini, T.; Thomas, R.; Mathew, B. Computational design and fabrication of enantioselective recognition sorbents for L-phenylalanine benzyl ester on multiwalled carbon nanotubes using molecular imprinting technology. Chinese J. Polym. Sci. 2019, 37, 1305–1318.

T Sajini, Renjith Thomas, Beena Mathew. Computational Design and Fabrication of Enantioselective Recognition Sorbents for L-phenylalanine Benzyl Ester on Multiwalled Carbon Nanotubes Using Molecular Imprinting Technology[J]. Chinese Journal of Polymer Science, 2019, 37(12): 1305-1318.
Sajini, T.; Thomas, R.; Mathew, B. Computational design and fabrication of enantioselective recognition sorbents for L-phenylalanine benzyl ester on multiwalled carbon nanotubes using molecular imprinting technology. Chinese J. Polym. Sci. 2019, 37, 1305–1318. DOI： 10.1007/s10118-019-2282-4.

T Sajini, Renjith Thomas, Beena Mathew. Computational Design and Fabrication of Enantioselective Recognition Sorbents for L-phenylalanine Benzyl Ester on Multiwalled Carbon Nanotubes Using Molecular Imprinting Technology[J]. Chinese Journal of Polymer Science, 2019, 37(12): 1305-1318. DOI： 10.1007/s10118-019-2282-4.

摘要

Abstract

Computational strategies have been employed to investigate the influence of the nature of monomers and cross-linker in order to design three dimensional imprinted polymers with selective recognition sites for L-phenylalanine benzyl ester (L-PABE) molecule. Here

computational chemistry methods were applied to screen the molar quantity of functional monomers that interact with one mole of the template molecule. Effects of the nature of functional monomer

cross-linker

and molar ratio were determined computationally using density functional calculations with B3LYP functional and generic 6-31G basis set. Methacrylic acid (MAA) and ethylene glycol dimethacrylate (EGDMA) were used as the functional monomer and crosslinking agent

respectively. L-PABE imprinted polymer layered on multiwalled carbon nanotube (MWCNT) and conventional bulk MIP were synthesised and characterized as well. To investigate the influence of pre-organization of binding sites on the selectivity of L-PABE

respective non-imprinted polymers were also synthesised. MWCNT-MIPs and MIPs exhibited the highest adsorption capacity towards L-PABE. The synthesized polymers revealed characteristic adsorption features and selectivity towards L-PABE in comparison with those of its enantiomer analogues.

关键词

Keywords

references

Ertürk, G.; Mattiasson, B . Molecular imprinting techniques used for the preparation of biosensors . Sensors , 2017 . 288 1 - 17 . .

Shah, N; Haneef, M; Park, J; Ul-Islam, M . A brief overview of molecularly imprinted polymers: From basics to applications . J. Pharm. Res. , 2012 . 5 3309 - 3317 . .

Ou, J.; Dong, J.; Tian, T.; Hu, J.; Ye, M.; Zou, H . Enantioseparation of tetrahydropalmatine and Tröger’s base by molecularly imprinted monolith in capillary electrochromatography . J. Biochem. Biophys. Methods , 2007 . 70 71 - 76 . DOI: 10.1016/j.jbbm.2006.07.003 http://doi.org/10.1016/j.jbbm.2006.07.003 .

Lu, Y.; Li, C.; Zhang, H.; Liu, X . Study on the mechanism of chiral recognition with molecularly imprinted polymers . Anal. Chim. Acta , 2003 . 489 33 - 43 . DOI: 10.1016/S0003-2670(03)00708-6 http://doi.org/10.1016/S0003-2670(03)00708-6 .

Mahony, J. O.; Karlsson, B. C. G.; Nicholls, I. A . Correlated theoretical, spectroscopic and X-ray crystallographic studies of a non-covalent molecularly imprinted polymerisation system . Analyst , 2007 . 132 1161 - 1168 . DOI: 10.1039/b706258c http://doi.org/10.1039/b706258c .

Sajini, T.; Gigimol, M. G.; Mathew, B . A brief overview of molecularly imprinted polymers supported on titanium dioxide matrices . Mater. Today Chem. , 2019 . 11 283 - 295 . DOI: 10.1016/j.mtchem.2018.11.010 http://doi.org/10.1016/j.mtchem.2018.11.010 .

Zhong, C.; Yang, B.; Jiang, X.; Li, J . Critical reviews in analytical chemistry current progress of nanomaterials in molecularly imprinted electrochemical sensing current progress of nanomaterials in molecularly imprinted electrochemical sensing . Crit. Rev. Anal. Chem. , 2018 . 48 15 - 32 . DOI: 10.1080/10408347.2017.1360762 http://doi.org/10.1080/10408347.2017.1360762 .

Rezaei, B.; Rahmanian, O . Direct nanolayer preparation of molecularly imprinted polymers immobilized on multiwalled carbon nanotubes as a surface-recognition sites and their characterization . J. Appl. Polym. Sci. , 2012 . 125 798 - 803 . DOI: 10.1002/app.v125.1 http://doi.org/10.1002/app.v125.1 .

Jacobs, C . Nanotube based electrochemical sensors for biomolecules . Anal. Chim. Acta , 2010 . 662 105 - 127 . DOI: 10.1016/j.aca.2010.01.009 http://doi.org/10.1016/j.aca.2010.01.009 .

Anirudhan, T. S.; Alexander, S . Synthesis and characterization of vinyl-functionalized multiwalled carbon nanotubes based molecular imprinted polymer for the separation of chlorpyrifos from aqueous solutions . J. Chem. Technol. Biotechnol. , 2013 . 88 1847 - 1858 . DOI: 10.1002/jctb.4039 http://doi.org/10.1002/jctb.4039 .

Xu, L.; Xu, Z . Molecularly imprinted polymer based on multiwalled carbon nanotubes for ribavirin recognition . J. Polym. Res. , 2012 . 19 1 - 6 . DOI: 10.1007/s10965-012-0001-8 http://doi.org/10.1007/s10965-012-0001-8 .

Kan, X.; Zhao, Y.; Geng, Z.; Wang, Z.; Zhu, J . Composites of multiwalled carbon nanotubes and molecularly imprinted polymers for dopamine recognition . J. Phys. Chem. C , 2008 . 112 4849 - 4854 . .

Scida, K.; Stege, P. W.; Haby, G.; Messina, G. A.; García, C. D . Recent applications of carbon-based nanomaterials in analytical chemistry . Anal. Chim. Acta , 2011 . 691 6 - 17 . DOI: 10.1016/j.aca.2011.02.025 http://doi.org/10.1016/j.aca.2011.02.025 .

Prasad, B. B.; Srivastava, A.; Pandey, I.; Tiwari, M. P . Electrochemically grown imprinted polybenzidine nanofilm on multiwalled carbon nanotubes anchored pencil graphite fibers for enantioselective micro-solid phase extraction coupled with ultratrace sensing of D- and L-methionine . J. Chromatogr. B , 2013 . 912 65 - 74 . DOI: 10.1016/j.jchromb.2012.10.010 http://doi.org/10.1016/j.jchromb.2012.10.010 .

Datsyuk, V.; Kalyva, M.; Papagelis, K.; Parthenios, J.; Tasis, D.; Siokou, A.; Kallitsis, I.; Galiotis, C . Chemical oxidation of multiwalled carbon nanotubes . Carbon , 2008 . 6 2 - 9 . .

Nicholls, I. A.; Andersson, H. S.; Golker, K.; Henschel, H.; Karlsson, B. C. G.; Olsson, G. D.; Rosengren, A. M.; Shoravi, S.; Suriyanarayanan, S.; Wiklander, J. G.; Wikman, S . Rational design of biomimetic molecularly imprinted materials: Theoretical and computational strategies for guiding nanoscale structured polymer development . Anal. Bioanal. Chem. , 2011 . 400 1771 - 1786 . DOI: 10.1007/s00216-011-4935-1 http://doi.org/10.1007/s00216-011-4935-1 .

Meier, F.; Schott, B.; Riedel, D.; Mizaikoff, B . Computational and experimental study on the influence of the porogen on the selectivity of 4-nitrophenol molecularly imprinted polymers . Anal. Chim. Acta , 2012 . 744 68 - 74 . DOI: 10.1016/j.aca.2012.07.020 http://doi.org/10.1016/j.aca.2012.07.020 .

Riahi, S.; Edris-Tabrizi, F.; Javanbakht, M.; Ganjali, M. R.; Norouzi, P . A computational approach to studying monomer selectivity towards the template in an imprinted polymer . J. Mol. Model. , 2009 . 15 829 - 836 . DOI: 10.1007/s00894-008-0437-2 http://doi.org/10.1007/s00894-008-0437-2 .

Cowen, T.; Karim, K.; Piletsky, S . Computational approaches in the design of synthetic receptors—A review . Anal. Chim. Acta , 2016 . 936 62 - 74 . DOI: 10.1016/j.aca.2016.07.027 http://doi.org/10.1016/j.aca.2016.07.027 .

Nicholls, I. A.; Chavan, S.; Golker, K.; Karlsson, C. G.; Olsson, G. D.; Rosengren, A. M . Theoretical and computational strategies for the study of the molecular imprinting process and polymer performance . Adv. Biochem. Eng. Biotechnol. , 2015 . 150 25 - 50 . .

Batra, D.; Shea, K. J . Combinatorial methods in molecular imprinting . Curr. Opin. Chem. Biol. , 2003 . 7 434 - 442 . DOI: 10.1016/S1367-5931(03)00060-7 http://doi.org/10.1016/S1367-5931(03)00060-7 .

Sajini, T.; Aravind, K.; Mathew, B . Theoretical and computational strategies for the fabrication of enantioselective recognition site on molecularly imprinted polymers . Int. J. Curr. Adv. Res. , 2017 . 6 6334 - 6336 . .

Nicholls, I. A.; Andersson, H. S.; Charlton, C.; Henschel, H.; Karlsson, B. C. G.; Karlsson, J. K.; Mahony, J. O.; Rosengren, A. M.; Rosengren, K. J.; Wikman, S . Theoretical and computational strategies for rational molecularly imprinted polymer design . Biosens. Bioelectron. , 2009 . 25 543 - 552 . DOI: 10.1016/j.bios.2009.03.038 http://doi.org/10.1016/j.bios.2009.03.038 .

Tadi, K. K.; Motghare, R. V . Computational and experimental studies on oxalic acid imprinted polymer . J. Chem. Sci. , 2013 . 125 413 - 418 . DOI: 10.1007/s12039-013-0381-2 http://doi.org/10.1007/s12039-013-0381-2 .

Riahi, S.; Eynollahi, S.; Ganjali, M. R.; Norouzi, P . Computational approach to investigation of template/monomer complex in imprinted polymers; dinitrobenzene sensor . Int. J. Electrochem. Sci. , 2010 . 5 509 - 516 . .

Khan, M. S.; Wate, P. S.; Krupadam, R. J . Combinatorial screening of polymer precursors for preparation of benzo . J. Mol. Model. , 2012 . 18 1969 - 1981 . DOI: 10.1007/s00894-011-1218-x http://doi.org/10.1007/s00894-011-1218-x .

Nicholls, I. A.; Karlsson, C. G.; Olsson, G, D.; Rosengren, A. M . Computational strategies for the design and study of molecularly imprinted materials . Ind. Eng. Chem. Res. , 2018 . 10 27 .

McCormick, T. M.; Bridges, C. R.; Carrera, E. I.; Dicarmine, P. M.; Gibson, G. L.; Hollinger, J.; Kozycz, L. M.; Seferos, D. S . Conjugated polymers: Evaluating DFT methods for more accurate orbital energy modeling . Macromolecules , 2013 . 46 3879 - 3886 . DOI: 10.1021/ma4005023 http://doi.org/10.1021/ma4005023 .

Singh, A. K.; Singh, M . Designing L-serine targeted molecularly imprinted polymer via theoretical investigation . J. Theor. Comput. Chem. , 2016 . 15 1650014 DOI: 10.1142/S0219633616500413 http://doi.org/10.1142/S0219633616500413 .

Mojica, E. R. E . Screening of different computational models for the preparation of sol-gel imprinted materials . J. Mol. Model. , 2013 . 19 3911 - 3923 . DOI: 10.1007/s00894-013-1928-3 http://doi.org/10.1007/s00894-013-1928-3 .

Silva, C. F.; Borges, K. B.; Soares, C . Rational design of a molecularly imprinted polymer for dinotefuran: Theoretical and experimental studies aimed at the development of an efficient adsorbent for microextraction by packed sorbent . Analyst , 2018 . 143 141 - 149 . DOI: 10.1039/C7AN01324H http://doi.org/10.1039/C7AN01324H .

Pardeshi, S.; Patrikar, R.; Dhodapkar, R.; Kumar, A . Validation of computational approach to study monomer selectivity toward the template Gallic acid for rational molecularly imprinted polymer design . J. Mol. Model. , 2012 . 18 4797 - 4810 . DOI: 10.1007/s00894-012-1481-5 http://doi.org/10.1007/s00894-012-1481-5 .

Acquaye, C. T. A.; Gorecki, M.; Wilchek, M.; Votano, J. R.; Rich, A . Antisickling activity of amino acid benzyl esters . Proc. Natl. Acad. Sci. , 1980 . 77 181 - 185 . DOI: 10.1073/pnas.77.1.181 http://doi.org/10.1073/pnas.77.1.181 .

Acquaye, C. T. A.; Young, J. D.; Ellory, J. C.; Gorecki, M.; Wilchek, M . Mode of transport and possible mechanism of action of L-phenylalanine benzyl ester as an anti-sickling agent . Biochim. Biophys. Acta , 1982 . 693 407 - 416 . DOI: 10.1016/0005-2736(82)90448-5 http://doi.org/10.1016/0005-2736(82)90448-5 .

Frisch, G. E. S. M. J.; Trucks, G. W.; Schlegel, H. B.; Robb, B. M. M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, H. P. H. G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Izmaylov, M. H. A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Ehara, T. N. M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Honda, J. Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, E. B. J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Kudin, J. N. K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Raghavachari, J. T. K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Cossi, J. B. C. M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Bakken, R. E. S. V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Yazyev, J. W. O. O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Martin, G. A. V. R. L.; Morokuma, K.; Zakrzewski, V. G.; Salvador, A. D. D. P.; Dannenberg, J. J.; Dapprich S.; Farkas, D. J. F. O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J. Gaussian 09 Revis. D.01, 2013 .

Dennington, R.; Keith, T.; Millam, J. Semichem Inc. Shawnee Mission. KS, 2016 .

Polimer, P.; Molekul, C . Synthesis and characterization of a molecularly imprinted polymer for Pb 2+ uptake using 2-vinylpyridine as the complexing monomer . Sains. Malaysiana , 2010 . 39 829 - 835 . .

Zakaria, N. D.; Yusof, N. A.; Haron, J.; Abdullah, A. H . Synthesis and evaluation of a molecularly imprinted polymer . Int. J. Mol. Sci. , 2009 . 10 354 - 365 . DOI: 10.3390/ijms10010354 http://doi.org/10.3390/ijms10010354 .

Zhang, W.; Li, Q.; Cong, J.; Wei, B.; Wang, S . Mechanism analysis of selective adsorption and specific recognition by molecularly imprinted polymers of Ginsenoside Re . Polymers , 2018 . 10 216 DOI: 10.3390/polym10020216 http://doi.org/10.3390/polym10020216 .

Yuan, H.; Ma, X.; Xu, Z . Pore structure analysis of PFSA/SiO 2 composite catalysts from nitrogen adsorption isotherms . Sci. China Chem. , 2011 . 54 257 - 262 . DOI: 10.1007/s11426-010-4185-7 http://doi.org/10.1007/s11426-010-4185-7 .

Li, S.; Huang, X.; Zheng, M.; Li, W.; Tong, K . Molecularly imprinted polymers: Thermodynamic and kinetic considerations on the specific sorption and molecular recognition . Sensors , 2008 . 8 2854 - 2864 . DOI: 10.3390/s8042854 http://doi.org/10.3390/s8042854 .

Karim, K.; Breton, F.; Rouillon, R.; Piletska, E. V.; Guerreiro, A.; Chianella, I.; Piletsky, S. A . How to find effective functional monomers for effective molecularly imprinted polymers? . Adv. Drug Deliver. Rev. , 2005 . 57 1795 - 1808 . DOI: 10.1016/j.addr.2005.07.013 http://doi.org/10.1016/j.addr.2005.07.013 .

Liu, J.; Wang, Y.; Tang, S . Theoretical guidance for experimental research of the dicyandiamide and methacrylic acid molecular imprinted polymer . New J. Chem. , 2017 . 41 13370 - 13376 . DOI: 10.1039/C7NJ00207F http://doi.org/10.1039/C7NJ00207F .

Muhammad, T.; Nur, Z.; Piletska, E. V.; Piletsky, S. A . Rational design of molecularly imprinted polymer: The choice of cross-linker . Analyst , 2012 . 137 2623 - 2628 . DOI: 10.1039/c2an35228a http://doi.org/10.1039/c2an35228a .

浏览量

195

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Molecular Designs of Sulfur-containing High Refractive Index and Abbe Number Polymers Using Density Functional Theory

Study on Catalytic Behavior of Iron-based Catalyst with IITP as Electron Donor in the Polymerization of Butadiene

Fabrication of Molecularly Imprinted Electrospun Nanofibers with Mono-amidoxime Functional Ligand for Efficient Decontamination of Toxic Organophosphates

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

Silk Sericin-inspired Poly-β-homoserine for Protein Protection