670
Views
3
CrossRef citations to date
0
Altmetric
Articles

Transition state analogue imprinted polymers as artificial amidases for amino acid p-nitroanilides: morphological effects of polymer network on catalytic efficiency

, &
Pages 1830-1837 | Received 14 Jul 2017, Accepted 16 Oct 2017, Published online: 13 Nov 2017

References

  • Vlatakis G, Andersson LI, Mosbach K, et al. Drug assay using antibody mimics made by molecular imprinting. Nature. 1993;361:645–647.
  • Chen L, Xu S, Li J. Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev. 2011;40:2922–2942.
  • Haupt K, Mosbach K. Molecularly imprinted polymers and their use in biomimetic sensors. Chem Rev. 2000;100:2495–2504.
  • Wulff G, Liu J. Design of biomimetic catalysts by molecular imprinting in synthetic polymers: the role of transition state stabilization. Acc Chem Res. 2012;45:239–247.
  • Alexander C, Davidson L, Hayes W. Stereoselective reduction of menthone by molecularly imprinted polymers. Tetrahedron. 2003;59:2025–2057.
  • Kawanami Y, Yunoki T, Nakamura A. Rationally designing active molecularly imprinted polymer toward a highly specific catalyst by using metal as an assembled pivot. J Mol Catal A Chem. 1999;145:107–110.
  • Ohkubo K, Urata K, Hirota S. Homogeneous esterolytic catalysis of a polymer prepared by molecular imprinting of a transition state analogue. J Mol Catal. 1994;93:189–193.
  • Wulff G, Gross T, Schonfeld R. Enzyme models based on molecularly imprinted polymers with strong esterase activity. Angew Chem Int Ed Engl. 1997;36:1962–1964.
  • Kim JM, Ahn KD, Wulff G. Cholesterol esterase activity of a molecularly imprinted polymer. Macromol Chem Phys. 2001;202:1105–1108.
  • Robinson KD, Mosbach K. Molecular imprinting of a transition state analogue leads to a polymer exhibiting esterolytic activity. J Chem Soc Chem Commun. 1989;28:969–970.
  • Liu XC, Mosbach K. Catalysis of benzisoxazole isomerization by molecularly imprinted polymers. Macromol Rapid Commun. 1998;19:671–674.
  • Carboni D, Flavin K, Resmini M, et al. The first example of molecularly imprinted nanogels with aldolase type I activity. Chemistry. 2008;14:7059–7065.
  • Ohkubo K, Urata Y, Hirota S, et al. Catalytic activities of novel L-histidyl group-introduced polymers imprinted by a transition state analogue in the hydrolysis of amino acid esters. J Mol Catal. 1995;101:L111–L114.
  • Lele BS, Kulkarni MG, Mashelkar RA. Molecularly imprinted polymer mimics of chymotrypsin: 2. Functional monomers and hydrolytic activity. React Funct Polym. 1999;40:215–229.
  • Corman ME, Akgol S. Preparation of molecular imprinted hydrophobic polymeric nanoparticles having structural memories for lysozyme recognition. Artif Cells Nanomed Biotechnol. 2012;40:245–255.
  • Akgonullu S, Yavuz H, Denizli A. Preparation of imprinted cryogel cartridge for chiral separation of L-phenylalanine. Artif Cells Nanomed Biotechnol. 2016;45:800–807.
  • Gokturk I, Uzek R, Denizli A, et al. Synthesis of a specific monolithic column with artificial recognition sites for L-glutamic acid via cryo-crosslinking of imprinted nanoparticles. Artif Cells Nanomed Biotechnol. 2015;44:1133–1140.
  • Ohkubo K, Urata Y, Yoshinaga K. Preparation and catalytic property of L-histidyl group-introduced, crosslinked poly(ethylene imine)s imprinted by a transition-state analogue of an esterolysis reaction. Polymer. 1994;35:5372–5374.
  • Mathew D, Thomas B, Devaky KS. Amidase activity of phosphonate analogue imprinted chymotrypsin mimics in shape-selective, substrate-specific and enantioselective amidolysis of L-phenylalanine-p-nitroanilides. J Mol Catal A: Chem. 2016;415:65–73.
  • Mathew D, Thomas B, Devaky KS. Phosphonate TSA-built macromatric polymer catalysts as chymotrypsin mimics for the amidolysis of amino acid p-nitroanilides:-Effect of the nature and extent of crosslinker on amidase activities. Polymer. 2017;111:285–296.
  • Mathew D, Thomas B, Devaky KS. Amidase activity of phosphonate TSA-built polymer catalysts derived from organic monomers in the amidolysis of amino acid p-nitroanilides. Appl Catal A: Gen. 2016;528:93–103.
  • Umpleby RJ, Rushton GT, Shah RN, et al. Recognition directed site-selective chemical modification of molecularly imprinted polymers. Macromolecules. 2001;34:8446–8452.
  • Haupt K, Dzgoev A, Mosbach K. Assay system for the herbicide 2,4-dichlorophenoxy acetic acid using a molecularly imprinted polymer as an artificial recognition element. Anal Chem. 1998;70:628–631.
  • Golker K, Nicholls IA. The effect of crosslinking density on molecularly imprinted polymer morphology and recognition. Eur Polym J. 2016;75:423–430.
  • Ohkubo K, Sawakuma K, Sagawa T. Shape- and stereo-selective esterase activities of cross-linked polymers imprinted with a transition-state analogue for the hydrolysis of amino acid esters. J Mol Catal. 2001;165:1–7.
  • Karmalkar RN, Kulkarni MG, Mashelkar RA. Molecularly imprinted hydrogels exhibit chymotrypsin-like activity. Macromolecules. 1996;29:1366–1368.
  • Ohkubo K, Funakoshi Y, Sagawa T. Catalytic activity of a novel water-soluble cross-linked polymer imprinted by a transition-state analogue for the stereoselective hydrolysis of enantiomeric amino acid esters. Polymer. 1996;37:3993–3995.
  • Emgenbroich M, Wulff G. A New Enzyme Model For Enantioselective Esterases Based On Molecularly Imprinted Polymers. Chem Eur J. 2003;9:4106–4117.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.