Bacterial conversion of alkylphosphonates to natural products via carbon-phosphorus bond cleavage

Abstract

The phosphorus-containing breakdown products of 0-alkyl alkylphosphonate toxicants, which are particularly resistant to cleavage at the C-P bond, were fully degraded to natural products by Pseudomonas testosteroni. When present as a sole and limiting phosphorus source, an 0-alkyl alkylphosphonate was attacked aerobically via release of the alkoxy group as the alcohol, followed by cleavage of the alkyl-phosphorus bond (methyl, ethyl, or propyl) to produce the respective alkane and an inorganic phosphorus compound that was detected as inorganic orthophosphate. The bacterium could not cleave the bonds of other carbon-heteroatoms (e.g., arsonates, sulfonates, and mercurials). This is the first report of the metabolism of simple, aliphatic alkylphosphonates and the first pathway described for an organophosphorus toxicant to yield exclusively natural products (i.e., alcohols, alkanes, and phosphate).