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Reference type: Journal
Authors: Belokon YN, Tararov VI, Savel'eva TF, Belikov VM
Article Title: Biomimetic approach to the design of a pyridoxal enzyme model 1. Hydrophilic polyacrylamide gel with stereochemically defined arrangements of salicaldehyde and lysine fragments.
Publication date: 1980
Journal: Makromolekulare Chemie-Macromolecular Chemistry And Physics
Volume: 181
Issue: (10)
Page numbers: 2183-2197.
DOI: 10.1002/macp.1980.021811015

Abstract: A polymeric gel in which salicylaldehyde and lysine moieties are capable of forming an internal aldimine at pH > 6,0 has been prepared by copolymerization of N-5-methacryloylaminosalicylidene-N-methacryloyl-(S)-lysinatocopper (II) (1a) with acrylamide and N,N'-methylenebisacrylamide in water with subsequent removal of the copper ions by 0,1 M HCl or the disodium salt of EDTA. The equilibrium formation constants of the internal aldimine are ca. 30 times (at pH 7,1) and ca. 100 times (at pH 9,2) higher than the equilibrium constants of the model reaction of Schiff base formation from 5-isobutyrylaminosalicylaldehyde (2) and Nt-isobutyryl-(S)-lysine (3). The -amino group of the lysine residue in the gel acts as a nucleophilic catalyst in the reaction of the salicylaldehyde moiety of the gel with semicarbazide. The reaction proceeds 5,3 times faster in the gel than in a model polymeric system which does not contain lysine moieties.


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