CHEMICAL TRANSFORMATIONS OF PYRIDOXAL AND PYRIDOXAL 5’-PHOSPHATE PRODUCTS WITH L-CYSTEINE, L-SERINE AND L-METHIONINE
Keywords:
pyridoxal , pyridoxal-5´-phosphate, cysteine, serine, methionine, kinetics.Abstract
The mechanisms of condensation of l-cysteine, l-methionine, and l-serine with
pyridoxal and pyridoxal-5-phosphate with l-cysteine were studied by the kinetic method. Unlike
methionine and serine, the condensation of cysteine with pyridoxal and transaldimination with
Npyridoxylidene-β-alanine involves intermediate formation of stable product having a thiazolidine ring. Its structure was determined by elemental analysis, UV, and IR spectroscopy, and quantum-chemical calculations. The thiazolidine fragment in the pyridoxal condensation product with
l-cysteine is turned through an angle of 90° with respect to the pyridine ring plane due to mutual
repulsion of the negatively charged oxygen atom in the ortho position of the pyridine ring and
sulfur and nitrogen atoms in the thiazolidine ring.
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