Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation

Article abstract of DOI:10.1021/ja00256a033

Utilization of aminomethyl-, N-methylaminomethyl-, N,N-dimethylaminomethyl-, and N-acetylaminomethylphosphonate by Escherichia coli as a sole source of phosphorus during growth resulted in the extracellular generation of N-methylacetamide, N,N-dimethylacetamide, trimethylamine, and N-methylacetamide, respectively.Product identification relied on synthesis of (13)C-enriched aminomethylphosphonates followed by (1)H NMR analysis of products isolated from the biodegradation of the labeled and unlabeled phosphorus sources.To circumvent the requirement of an intact cell for carbon to phosphorus bond degradation, transposon mutagenesis was exploited as a complement to the chemical analysis.E. coli K-12 were infected with λ<*>Tn5.Colonies resistant to kanamycin were selected and then screened for loss of the ability to use ethylphosphonate as a sole source of phosphorus.The mutant identified, E. coli SL724, was also unable to degrade aminomethylphosphonates.This combination of chemical and mutagenic analysis points toward a shared mechanism between alkyl- and aminomethylphosphonate biodegradation.