Isolation of 2-Aminoethane Phosphonic Acid from Rumen Protozoa

Horiguchi, Masaaki; Kandatsu, Makoto

doi:10.1038/184901b0

Cited by 390 publications

(154 citation statements)

References 3 publications

Supporting

Mentioning

150

Contrasting

Unclassified

Order By: Relevance

“…However, phosphonic acids, a class of organophosphorus compounds containing a direct carbon-phosphorus bond, are also found in nature (14,21). The initial discovery of a natural phosphonic acid product, 2-aminoethylphosphonic acid, in 1959 (18) is relatively recent compared with the history of research in biological organophosphate esters. Since that time dozens of naturally occurring C-P compounds have been discovered (17).…”

mentioning

confidence: 99%

Bacterial carbon-phosphorus lyase: products, rates, and regulation of phosphonic and phosphinic acid metabolism

Wackett¹,

Shames²,

Venditti³

et al. 1987

J Bacteriol

169

115

View full text Add to dashboard Cite

Carbon-phosphorus bond cleavage activity, found in bacteria that utilize alkyl-and phenylphosphonic acids,has not yet been obtained in a cell-free system. Given this constraint, a systematic examination of in vivo C-P lyase activity has been conducted to develop insight into the C-P cleavage reaction. Six bacterial strains were obtained by enrichment culture, ideptified, and characterized with respect to their phosphonic acid substrate specificity. One isolate, Agrob4acterium radiobacter, was shown to cleave the carbon-phosphorus bond of a wide range of substrates, including fosfomycin, glyphosate, and dialkyl phosphinic acids. Furthermore, this organism processed vinyl-, propenyl-, and prQpynylphosphonic acids, a previously uninvestigated group, to ethylene, propene, and propyne, respectively. A determination of product stoichiometries revealed that both C-P bonds of dimethylphosphinic acid are cleaved quantitatively to methane and, furthermore, that the extent of C-P bond cleavage correlated linearly with the specific growth rate for a range of substrates. The broad substrate specificity of Agrobacterium C-P lyase and the comprehensive characterization of the in vivo activity make this an attractive system for further biochemical and mechanistic experiments. In addition, the failure to observe the activity in a group of gram-positive bacteria holds open the possibility that a periplasmic component may be required for in vivo expression of C-P lyase activity.Living systems contain organophosphorus mostly in the form of oxygen esters, diesters, and anhydrides of phosphoric acid. However, phosphonic acids, a class of organophosphorus compounds containing a direct carbon-phosphorus bond, are also found in nature (14, 21). The initial discovery of a natural phosphonic acid product, 2-aminoethylphosphonic acid, in 1959 (18) is relatively recent compared with the history of research in biological organophosphate esters. Since that time dozens of naturally occurring C-P compounds have been discovered (17). The biosynthesis of the C-P bond has been documented in protozoa, fungi, and molluscs (16, 37). The importance of C-P bonds in these invertebrates is underscored by the observation that 50 to 75% of the cilia phospholipids of Tetrahymena are phosphonolipids (22).Given the biosynthetic accessibility of the C-P linkage it is almost axiomatic that bacteria would have evolved the ability to catabolize phosphonic acids. Indeed, by enrichment culture bacteria have been obtained that utilize 2-aminoethylphosphonic acid, the most abundant naturally occurring phosphonic acid, as the sole source of phosphorus, nitrogen, and carbon (4). The biochemistry of this process was first investigated in Bacillus cereus, where 2-aminoethylphosphonic acid was shown to undergo transamination to yield phosphonoacetaldehyde followed by hydrolysis to acetaldehyde and Pi (25). The hydrolytic cleavage step is catalyzed by phosphonoacetaldehyde hydrolyase (26), an enzyme given the trivial name of phosphonatase (equation 1).2-phosphonatase OHCCH...

show abstract

mentioning

confidence: 99%

Bacterial carbon-phosphorus lyase: products, rates, and regulation of phosphonic and phosphinic acid metabolism

Wackett¹,

Shames²,

Venditti³

et al. 1987

J Bacteriol

169

115

View full text Add to dashboard Cite

show abstract

“…Indeed, early evidence for natural C-P compounds was based upon finding organophosphorus that was released during combustion which resisted strong-acid and strongbase hydrolysis (17). The first natural C-P compound was isolated from ciliates and identified as 2-aminoethylphosphonate (AEPn) in 1959 (16). AEPn is a structural analog of the ethanolamine Pi moiety in phospholipids.…”

mentioning

confidence: 99%

Mapping and molecular cloning of the phn (psiD) locus for phosphonate utilization in Escherichia coli

Wanner

Boline

1990

J Bacteriol

View full text Add to dashboard Cite

show abstract

“…With minor exceptions, the polar lipid composition of Sinonovacula constricta was identical to that of other invertebrates. 24 "'29) Phosphatidylethanolamine (spot 1,25.5%) appears to be present in large amounts together with small amounts of phosphatidylcholine (spot 2, 9.5%) and phosphatidylserine '(spot 4 Ceramide aminoethylphosphonate (spot 1), hydroxy fatty acid containing ceramide aminoethylphosphonate (spot 2) and sphingomyelin (spot 3) consisted of 75.8, 12.3 and 11.9% of the sphingolipid phosphorus, respectively.…”

Section: Resultsmentioning

confidence: 99%

Occurrence of Ceramide Aminoethylphosphonate in Edible Shellfish, AGEMAKI,Sinonovacula constricta

Tamari

Kandatsu

1986

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

Isolation of 2-Aminoethane Phosphonic Acid from Rumen Protozoa

Cited by 390 publications

References 3 publications

Bacterial carbon-phosphorus lyase: products, rates, and regulation of phosphonic and phosphinic acid metabolism

Bacterial carbon-phosphorus lyase: products, rates, and regulation of phosphonic and phosphinic acid metabolism

Mapping and molecular cloning of the phn (psiD) locus for phosphonate utilization in Escherichia coli

Occurrence of Ceramide Aminoethylphosphonate in Edible Shellfish, AGEMAKI,Sinonovacula constricta

Contact Info

Product

Resources

About