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Influence of the side chain on the stability of Schiff‐bases formed between pyridoxal 5′‐phosphate and amino acids
Author(s) -
Vazquez M. A.,
Muñoz F.,
Donoso J.,
Blanco F. García
Publication year - 1990
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.550220903
Subject(s) - chemistry , hydrolysis , imine , pyridoxal , amino acid , amine gas treating , phosphate , side chain , medicinal chemistry , reaction rate constant , ionic bonding , schiff base , organic chemistry , stereochemistry , kinetics , ion , catalysis , biochemistry , polymer , physics , quantum mechanics
The stability of some Schiff‐bases formed between PLP and different amino acids has been investigated in a wide range of pH. The kinetic constants of formation of these compounds and their hydrolysis rate constants have been determined. Results show that the α‐position of the carboxyl group of amino acid plays an important role on the mechanism of water attack upon the CNbond. The absence of ionic groups in the surroundings of that bond must be an important factor of stability. Bulky hydrophobic substituents in the amino acid, near the amine part, protect the imine bond against hydrolysis.