DOI QR코드

DOI QR Code

Polymer Catalysts by Molecular Imprinting: A Labile Covalent Bonding Approach


Abstract

An imprinting technique with labile covalent interactions has been developed in the design of new polymer catalysts. The template monomer 2 was prepared and copolymerized with DVB or EDMA to provide the polymer with a cavity having the shape of th e transition state of the reaction as well as binding sites for the substrate and catalytic functionalities. The rate of hydrolysis of diphenyl carbonate (1) in the presence of the imprinted polymer IP-DVB-THF was found to be 120 times faster than the background uncatalyzed reaction. A Km of 32 mM and a kcat of 1.8 ${\times}$ 10-3min-1 were observed from Michaelis-Menten kinetics with the imprinted polymer IP-DVB-THF.

Keywords

References

  1. Chemtech Wulff, G.
  2. Angew. Chem. Int. Ed. Engl. v.34 Wulff, G. Angew.
  3. Trends Polym. Sci. v.2 Shea, K. J.
  4. Trends Biochem. Sci. v.19 Mosbach, K.
  5. Adv. Polym. Sci. v.123 Steinke, J.; Sherrington, D. C.; Dunkin, I. R.
  6. Bull. Korean Chem. Soc. v.13 Kim, J.-M.; Chong, B.-O.; Ahn, K.-D.
  7. Angew. Chem. Int. Ed. Engl. v.36 Wulff, G.; Gross, T.; Schonfeld, R.
  8. Macromol. Rapid Commun. v.19 Liu, X.-C.; Mosbach, K.
  9. J. Am. Chem. Soc. v.116 Beach, J. V.; Shea, K.-J.
  10. Macromolecules v.29 Karmalkar, R. N.; Kulkarni, M. G.; Mashelkar, R. A.
  11. Tetrahedron: Asymmetry v.5 Sellergren, B.; Shea, K. J.
  12. Polymer v.35 Ohkubo, K.; Urata, Y.; Honda, Y.; Nakashima, Y.; Yoshinaga, K.
  13. Science v.252 Review see e.g. Lerner, R. A.; Benkovic, S. J.; Schulz, R. G.
  14. Covalent imprinting with a 4-hydroxystyrene derivative for catalyst design has been reported by Shea et al. (ref. 11)

Cited by

  1. Molecularly Imprinted Polymers Having Amidine and Imidazole Functional Groups As an Enzyme-Mimetic Catalyst for Ester Hydrolysis vol.10, pp.2, 2001, https://doi.org/10.1007/bf03218301
  2. Synthesis and Application of Tetracycline Imprinted Polymer vol.43, pp.6, 2001, https://doi.org/10.1080/00032710903491039
  3. Geometrical effect of 3D-memory cavity on the imprinting efficiency of transition-state analogue-built artificial hydrolases vol.75, pp.9, 2001, https://doi.org/10.1007/s00289-017-2237-2
  4. Design, synthesis and characterization of enzyme-analogue-built polymer catalysts as artificial hydrolases vol.47, pp.1, 2001, https://doi.org/10.1080/21691401.2019.1576703