The microbial metabolism of acetophenone. Metabolism of acetophenone and some chloroacetophenones by an Arthrobacter species.
1. An organism that utilizes acetophenone as sole source of carbon and energy was isolated in pure culture and tentatively identified as an Arthrobacter sp. 2. Cell-free extracts of the acetophenone-grown organism contained an enzyme, acetophenone oxygenase, that catalysed an NADPH-dependent consumption of O(2) in the presence of the growth substrate; approx. 1mol of O(2) and 1mol of NADPH were consumed per mol of acetophenone oxidized. 3. Cell-free extracts also contained an enzyme capable of the hydrolysis of phenyl acetate to phenol and acetate. The amount of this esterase was increased markedly by growth on acetophenone. 4. The observed products of the acetophenone oxygenase reaction by crude cell-free extracts were phenol and acetate. However, inhibition of the phenyl acetate esterase by paraoxon resulted in the formation of phenyl acetate from acetophenone. 5. A degradative sequence is proposed in which acetophenone is metabolized by an oxygen-insertion reaction to form phenyl acetate. Further metabolism occurs by hydrolysis of this ester. 6. The organism and extracts were shown to metabolize chlorinated acetophenones. The environmental implications of this observation are discussed.
D000098:Acetophenones / Q000378:metabolism*; D001173:Arthrobacter / Q000201:enzymology / Q000378:metabolism*; D002474:Cell-Free System; D004950:Esterases / Q000037:antagonists & inhibitors / Q000378:metabolism; D009249:NADP / Q000378:metabolism; D010101:Oxygen Consumption; D010105:Oxygenases / Q000378:metabolism; D010261:Paraoxon / Q000494:pharmacology; D010648:Phenylacetates / Q000378:metabolism; D002721:omega-Chloroacetophenone / Q000378:metabolism
D000098:Acetophenones; D010648:Phenylacetates; D009249:NADP; D002721:omega-Chloroacetophenone; D010105:Oxygenases; D004950:Esterases; D010261:Paraoxon