Degradation of substituted mandelic acids by meta fission reactions.
A strain of Acinetobacter lwoffii degraded 4-hydroxymandelic and 4-hydroxy-3-methoxymandelic acids to their corresponding benzoates, which were then hydroxylated by specific monooxygenases to yield, respectively, protocatechuic and 3-O-methylgallic acids; these were substrates for meta fission dioxygenases. The product formed from 3-O-methylgallate underwent slow spontaneous cyclization at pH 7 to release methanol.
D000150:Acinetobacter / Q000201:enzymology / Q000378:metabolism*; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D062385:Hydroxybenzoates / Q000378:metabolism; D008333:Mandelic Acids / Q000378:metabolism*; D000432:Methanol / Q000378:metabolism; D010105:Oxygenases / Q000378:metabolism; D014642:Vanilmandelic Acid / Q000378:metabolism*
D062385:Hydroxybenzoates; D008333:Mandelic Acids; C014600:4-hydroxymandelic acid; C009091:protocatechuic acid; D014642:Vanilmandelic Acid; D005707:Gallic Acid; C025525:3-O-methylgallic acid; D010105:Oxygenases; D000432:Methanol