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The rational use of hydrophobic effect‐based recognition in molecularly imprinted polymers
Author(s) -
Piletsky Sergey A.,
Andersson Håkan S.,
Nicholls Ian A.
Publication year - 1998
Publication title -
journal of molecular recognition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.401
H-Index - 79
eISSN - 1099-1352
pISSN - 0952-3499
DOI - 10.1002/(sici)1099-1352(199812)11:1/6<94::aid-jmr398>3.0.co;2-c
Subject(s) - molecularly imprinted polymer , chemistry , moiety , molecular recognition , hydrophobic effect , monomer , polymer , cyclodextrin , molecular imprinting , selectivity , aqueous solution , polymerization , combinatorial chemistry , polymer chemistry , isothermal titration calorimetry , organic chemistry , molecule , catalysis
A novel molecularly imprinted polymer (MIP) system selective for D ‐phenylalanine is described where polymerization is performed in aqueous solution. The unique polymer system comprises a hydrophobic moiety‐selective functional monomer, polymerizable β‐cyclodextrin, an electrostatic interacting functional monomer, 2‐acryloylamido‐2‐methylpropane sulfonic acid (AMPSA), and the crosslinking agent N,N′ ‐diacryloylpiperazine. Chromatographic evaluation of polymer–ligand recognition characteristics demonstrated ligand selectivity by the MIP and that optimal recognition was achieved through a balance of hydrophobic and electrostatic ligand–polymer interactions, indicating that recognition in these systems is regulated by enthalpy–entropy compensation. The imprinting effect was shown to be sufficient to reverse the inherent selectivity of cyclodextrin for L ‐phenylalanine. Copyright © 1998 John Wiley & Sons, Ltd.