Kinetic Study of the Schiffbase Formation between Glycine and Pyridoxal.pdfVIP

J. CHEM. SOC. PERKIN TRANS. 11 1989 1617 Kinetic Study of the Schiff-base Formation between Glycine and Pyridoxal 5- Phosphate (PLP), Pyridoxal (PL), and 5-Deoxypyridoxal (DPL) Miguel Angel Vazquez,a Gerard0 Echevarria,b Francisco MuEio~,~**Josefa Donoso,a and Francisco Garcia Blanco a Departamento de Quimica, Facultad de Ciencias, Universidadde las lslas Baleares, 07071 Palma de Mallorca, Spain Dpto. de Quimica Fisica, Facultad de Ciencias, Universidadde Alcala de Henares, Spain lnstituto de Quimica Fisica Rocasolano, C.S.I.C.Madrid, Spain The formation of Schiff bases between pyridoxal 5-phosphate (PLP), pyridoxal (PL), 5- deoxypyridoxal (DPL), and glycine has been investigated as a function of proton concentration at 25 C and 0.1 rnol dm-3 ionic strength. Ionization constants as well as equilibrium and microscopic kinetic constants of the ionic species present in solution have been determined. The results show that all the protonatable groups of the aldehyde molecule are involved in the intramolecular acidic catalysis of the dehydration process undergone by the a- hydroxyamine intermediate. Results also reveal that the formation of Schiff base with pyridoxal is greatly affected by the formation of the cyclic hemiacetal of this aldehyde. Pyridoxal 5-phosphate (PLP) is one of the active forms of the H, //o vitamin B, group, and it is involved in many enzymic reactions. C In PLP-dependent enzymes, coenzyme (PLP) is bound to protein through a Schiff-base linkage with the amine terminal group of a lysine residue.** Schiff bases of PLP an