PYRIDOXAL PHOSPHATE .2. BENZENE ANALOGS . 2-FORMYLPHENOXYACETIC ACIDS AS POTENTIAL ANTIMETABOLITES OF PYRIDOXAL PHOSPHATE

To determine if simple benzene compounds have potential as inhibitory analogs of pyridoxal phosphate (PPal), a series of substituted 2-formylphenoxyacetic acids has been synthesized and evaluated enzymically on tryosine decarboxylase apoenzyme (TDC). Three halo acids, 4,6-dichloro-, 3,4,6-trichloro-, and 4,6-dibromo-2-formylphenoxyacetic acids, were the most inhibitory analogs, ([I]/[S])0.5 = 2000-13,000, and were competitive with PPal. The 2-formyl group and the unsubstituted oxyacetic, acid function were both required for inhibitory effectiveness. 4-Nitrosalicylaldehyde and other simple salicylaldehydes were inelTeciive as inhibitors of TDC. it is suggested that the inhibitory compounds may bind to the PPal binding site or to the tyrosine binding site of TDC. © 1969, American Chemical Society. All rights reserved.