Radicals in decarboxylation of 2-arylacetates? The formations of Toluene from Phenylacetate, p-Cresol from p-Hydroxiphenylacetate and Skatole from Indoleacetate

• Applicant: Professor Dr. Thorsten Selmer (†)
• Subject Area: Metabolism, Biochemistry and Genetics of Microorganisms
• Term: from 1999 to 2007
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 5178026

In living organisms, the aromatic compounds toluene (methylbenzene), skatole (3-methylindole) and p-cresol (4-methylphenol) are derived from decarboxylation of phenylacetate, indoleacetate and p-hydroxyphenylacetate, respectively. At present time almost nothing is known about the enzymes producing these compounds, which are detrimental to human and animal health. The structures of the arylacetic acids suggest radical mechanisms in the catalysis of decarboxylation. A better understanding of the processes requires the purification and biochemical characterisation of the enzymes which carry out the decarboxylation of arylacetic acids in vivo. The molecular cloning of the genes encoding the proteins and the production of the proteins in sufficient amounts will allow a more detailed analysis of such enzymes. These investigations must consider the mechanistical properties as well as the specific inhibition of the enzymes by simple compounds which may allow a decrease in the level of p-cresol and skatole in the used air of mass cattle breeding facilities reducing the hazards and malodor accompanied with such installations.

• DFG Programme: Priority Programmes
• Subproject of: SPP 1071: Radikale in der enzymatischen Katalyse