Chemical transformation ofS‐benzylO‐ethyl phenylphosphonothiolate (Inezin®) by ultraviolet light

Murai, Toshinobu; Tomizawa, Chōjirō

doi:10.1080/03601237609372034

Cited by 16 publications

(7 citation statements)

References 6 publications

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“…2 A phosphonate motif is present in biomolecules which can act as inhibitors of certain biosynthetic pathways and can be degraded only by some prokaryotic microorganisms. 3 The high chemical stability of phosphonates, together with their resistance to biodegradation, makes this class of compounds of particular interest for the drug design.…”

Section: Introductionmentioning

confidence: 99%

Efficient and ‘green’ microwave-assisted synthesis of haloalkylphosphonates via the Michaelis–Arbuzov reaction

et al. 2011

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This paper deals with a novel, efficient and environmentally friendly synthesis of dialkyl haloalkylphosphonates via a microwave-assisted Michaelis-Arbuzov reaction. The approach is solventless, requires only one equivalent of each of the starting compounds, and provides high yields of pure products from which the impurities are easy to remove. The process has been optimised for batch and flow reactors and is especially profitable for the production of key intermediates in synthesis of Ethephon or acyclic nucleoside phosphonates such as adefovir, tenofovir, and cidofovir.

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Section: Introductionmentioning

confidence: 99%

Efficient and ‘green’ microwave-assisted synthesis of haloalkylphosphonates via the Michaelis–Arbuzov reaction

et al. 2011

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“…The recent appearance of glyphosate resistant recombinant plants resulted in the escalated application of glyphosate containing herbicides and, subsequently, to the extension of the pollution sites [2]. Unlike the easily degradable C-O-P ester bond in phosphates, the C-P bond in the phosphonates is resistant to physicochemical factors [3,4]. However, under certain conditions, it may be cleaved by the microbial enzymatic systems [5,6].…”

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confidence: 99%

Biodegradation of glyphosate by soil bacteria: Optimization of cultivation and the method for active biomass storage

et al. 2012

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Conditions for obtaining the active biomass of Ochrobactrum anthropi GPK 3 and Achromobacter sp. Kg 16, bacteria which are able to degrade the herbicide glyphosate (N phosphonomethylglycine), were investigated. In the batch culture, degradation was most effective in the medium with pH 6.0-7.0 and aera tion at 10-60% of air saturation supplemented with glutamate and ammonium chloride as sources of carbon and nitrogen, respectively. Due to the adaptation of the cells and induction of the relevant enzymatic systems, the inoculum grown in the presence of glyphosate exhibited 1.5-2 fold higher efficiency of xenobiotic deg radation than that grown with other sources of phosphorus (orthophosphate and methylphosphonic acid). The efficiency of the toxicant decomposition increased with an increase in a specific load of glyphosate, which the cells were subjected to during the initial stage of growth. The specific load was regulated both by the initial cell concentration and the concentration of the phosphorus source, and the effect was probably determined by its availability to microorganisms. Storage of the liquid biopreparation as a paste with stabiliz ers (ascorbate, thiourea, and glutamate) at room temperature for 50 days resulted in high level of bacteria via bility and a degrading activity approximately equal to that obtained when the bacteria were maintained on the agar medium containing glyphosate at 4°C with monthly transfers to the fresh culture medium.

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“…With certain exceptions, the C-P bond is highly resistant to chemical hydrolysis (4), thermal decomposition (4), and photolysis (17); hence, biological cleavage of the C-P bond in natural habitats assumes importance to prevent the accumulation of phosphonates. Cleavage of the C-P bond is apparently limited to certain microorganisms (8,16).…”

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Phosphonate utilization by bacteria

Cook¹,

Daughton²,

Alexander³

1978

J Bacteriol

127

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Bacteria able to use at least one of 13 ionic alkylphosphonates or O-alkyl or O,O-dialkyl alkylphosphonates as phosphorus sources were isolated from sewage and soil. Four of these isolates used 2-aminoethylphosphonic acid (AEP) as a sole carbon, nitrogen, and phosphorus source. None of the other phosphonates served as a carbon source for the organisms. One isolate, identified as Pseudomonas putida, grew with AEP as its sole carbon, nitrogen, and phosphorus source and released nearly all of the organic phosphorus as orthophosphate and 72% of the AEP nitrogen as ammonium. This is the first demonstration of utilization of a phosphonoalkyl moiety as a sole carbon source. Cell-free extracts of P. putida contained an inducible enzyme system that required pyruvate and pyridoxal phosphate to release orthophosphate from AEP; acetaldehyde was tentatively identified as a second product. Phosphite inhibited the enzyme system.

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Chemical transformation ofS‐benzylO‐ethyl phenylphosphonothiolate (Inezin^®) by ultraviolet light

Cited by 16 publications

References 6 publications

Efficient and ‘green’ microwave-assisted synthesis of haloalkylphosphonates via the Michaelis–Arbuzov reaction

Efficient and ‘green’ microwave-assisted synthesis of haloalkylphosphonates via the Michaelis–Arbuzov reaction

Biodegradation of glyphosate by soil bacteria: Optimization of cultivation and the method for active biomass storage

Phosphonate utilization by bacteria

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