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Synthesis, post‐modification and characterization of linear polystyrene‐based supports for interaction with immobilized biocatalysts
Author(s) -
Petenzi Michele,
Bavaro Teodora,
Cornaggia Claudio,
Ubiali Daniela,
Pregnolato Massimo,
Pasini Dario
Publication year - 2012
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.4307
Subject(s) - polystyrene , mandelic acid , polymer , polymer chemistry , chemistry , polymerization , nitroxide mediated radical polymerization , radical polymerization , chain transfer , chemical modification , organic chemistry , combinatorial chemistry
A series of linear polystyrene‐based supports has been synthesized using conventional or controlled (reversible addition fragmentation chain transfer or nitroxide‐mediated) free radical polymerizations, in order to modulate their molecular weight characteristics. Polymer post‐modification via esterification of the primary hydroxyl alcohol functionalities, pendant from the polymer backbone, with a mandelic acid derivative introduces efficiently (>85% yield) racemic, enzyme‐cleavable moieties. A study of the interactions of these polymeric substrates with immobilized penicillin G acylase, in mixed organic/aqueous buffer solvent systems, results in a modest enantioselectivity (comparable with that of racemic mandelic acid methyl ester), but reveals that the biocatalytically active moieties on the linear polymers can be cleaved with first‐order rate kinetics, as observed with small molecules in solution; the reaction rates (which can differ by more than one order of magnitude) are influenced both by the synthetic polymer length and by the polymer structure resulting from the method of polymerization used. Copyright © 2012 Society of Chemical Industry