Immobilization of the acylase from Escherichia coli on glyoxyl-agarose gives efficient catalyst for the synthesis of cephalosporins

Enzyme and Microbial Technology
Ilona EstruchM Terreni

Abstract

The catalytic properties of penicillin G acylase (PGA) from Escherichia coli, when used in kinetically controlled N-acylation (kcNa) of cephalosporanic nuclei, can be strongly influenced by the moiety in 3-position of the cephem structure. In the synthesis of Cefonicid (1c), the adsorption of the cephalosporanic nucleus (7-SACA) in the PGA active site appeared sensitively increased by a positive ionic interaction between an arginine (ArgA145) in the enzyme active site and the sulphonic group of the β-lactam structure. Interestingly, when PGA was immobilized on solid supports, any effect depending on the substrate structure resulted minimized; the catalytic properties of this enzyme were affected with different outcomes depending on the type of matrix and binding chemistry. The PGA immobilized on glyoxyl-agarose (hydrophilic support activated with aldehyde groups) resulted in a good catalyst when used in kinetically controlled N-acylation of different cephalosporanic nuclei. This derivatives allow much better Vs/Vh(1) (defined as the ratio between the rate of synthesis and the rate of hydrolysis of the acylating agent) than the same enzyme immobilized on Eupergit C, an acrylic hydrophobic supports activated with epoxy groups. Th...Continue Reading

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Citations

Jul 12, 2008·Applied Biochemistry and Biotechnology·Andrés IllanesCarolina Aguirre
Jun 2, 2009·Applied Biochemistry and Biotechnology·H V Adikane, D M Thakar
Jan 22, 2014·Applied Microbiology and Biotechnology·Helena MarešováPavel Kyslík
Nov 23, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Paolo BonomiDaniela Ubiali
Jul 16, 2010·Biotechnology and Bioengineering·Susana M S A BernardinoLuís P Fonseca
Aug 28, 2015·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Xiaoli WangAnfu Yan
Aug 11, 2021·International Journal of Biological Macromolecules·Veymar G Tacias-PascacioRoberto Fernandez-Lafuente

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