Enzymatic release of halogens or methanol from some substituted protocatechuic acids.
Four strains of gram-negative bacteria capable of growing at the expense of 5-chlorovanillate were isolated from soil, and the metabolism of one strain was studied in particular detail. In the presence of alpha, alpha'-bipyridyl, a suspension of 5-chlorovanillate-grown cells accumulated 5-chloroprotocatechuate from 5-chlorovanillate; in the absence of inhibitor these compounds, and various other 5-substituted protocatechuates and vanillates, were oxidized to completion. Cell suspensions of this strain grown on 5-chlorovanillate or vanillate released chloride quantitatively from 5-chlorovanillate and released methanol from syringate. Extracts of cells grown with 4-hydroxybenzoate, vanillate, or syringate possessed high levels of both protocatechuate 4,5-dioxygenase and 2-pyrone-4,6-dicarboxylate hydrolase; extracts from acetate-grown cells did not. Protocatechuate 4,5-dioxygenase, purified from strains that could grow with 5-chlorovanillate, oxidized 5-halogeno-protocatechuates and 3-O-methylgallate with the formation of 2-pyrone-4,6-dicarboxylate. A crude extract converted 5-chloroprotocatechuate into pyruvate plus oxaloacetate. On the basis of these observations, a meta-fission reaction sequence is proposed for the bacterial degradation of vanillate and protocatechuate substituted at C-5 of the benzene ring with halogen or methoxyl.
D002712:Chlorides / Q000378:metabolism; D062385:Hydroxybenzoates / Q000378:metabolism*; D000432:Methanol / Q000378:metabolism; D010071:Oxaloacetates / Q000378:metabolism; D010084:Oxidation-Reduction; D011549:Pseudomonas / Q000378:metabolism*; D011773:Pyruvates / Q000378:metabolism; D014641:Vanillic Acid / Q000031:analogs & derivatives / Q000378:metabolism
D002712:Chlorides; D062385:Hydroxybenzoates; D010071:Oxaloacetates; D011773:Pyruvates; C009091:protocatechuic acid; D014641:Vanillic Acid; D000432:Methanol