Bacterial conversion of alkylphosphonates to natural products via carbon-phosphorus bond cleavage
Author(s) -
Christian G. Daughton,
Alasdair M. Cook,
Martin Alexander
Publication year - 1979
Publication title -
journal of agricultural and food chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.203
H-Index - 297
eISSN - 1520-5118
pISSN - 0021-8561
DOI - 10.1021/jf60226a005
Subject(s) - chemistry , phosphorus , bond cleavage , carbon fibers , cleavage (geology) , organic chemistry , environmental chemistry , catalysis , biology , materials science , paleontology , fracture (geology) , composite number , composite material
The phosphorus-containing breakdown products of 0-alkyl alkylphosphonate toxicants, which are particularly resistant to cleavage a t 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 (Le., alcohols, alkanes, and phosphate).
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