Kinetics of the Hydrolysis of Phosphate Esters

Bel’skii, V. E.

doi:10.1070/rc1977v046n09abeh002175

Cited by 34 publications

(8 citation statements)

References 68 publications

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“…Catalyzed by more or less specific enzymes (phosphatases), − the phosphoester hydrolysis has been a well-known process for many decades and the related thermodynamic and kinetic aspects have been the target of a huge number of studies. , In principle, the phosphoester hydrolysis may proceed through two distinct mechanisms classified as associative or dissociative. The former implies the attack from a suitable nucleophile (such as a hydroxide ion) to the phosphorus nucleus, thus leading to a phosphorane intermediate which in turn eliminates an alkoxide as a leaving group.…”

Section: Resultsmentioning

confidence: 99%

Orientation and Specific Interactions of Nucleotides and Nucleolipids Inside Monoolein-Based Liquid Crystals

et al. 2009

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The entrapment of AMP, GMP, CMP, and UMP nucleotides along with two different AMP-based nucleolipids (hydrophobically functionalized nucleotides) inside the liquid crystalline phases of the monoolein/water system is investigated through optical microscopy, small-angle X-ray diffraction (SAXRD), and nuclear magnetic resonance (NMR) techniques. As ascertained mainly through (31)P NMR experiments, when included within the cubic phase, the various nucleotides undergo a slow hydrolysis of the sugar-phosphate ester bond, induced by specific interactions at the monoolein-water interface. Upon aging, the degradation of the nucleotides causes a cubic-to-hexagonal phase transition. Differently, neither hydrolysis nor alterations of the monoolein self-assembly are observed when the nucleotides are included as lipid derivatives within the cubic liquid crystalline phase. A model that explains both the hydrolysis and the consequent phase transition is presented.

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Section: Resultsmentioning

confidence: 99%

Orientation and Specific Interactions of Nucleotides and Nucleolipids Inside Monoolein-Based Liquid Crystals

et al. 2009

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“…Micellar catalysis can be considered the simplest analogue of biocatalysis and therefore is of particular interest. − The reaction under study exhibits properties that make it an excellent probe for mixed micellar influence, since its rate is extremely sensitive to the medium effect. The hydrolysis of phosphorus acid esters has been studied in detail in aqueous and single micellar solutions. − The reaction proceeds through breaking the P−O bond, which is facilitated by the presence of electron-withdrawing groups. Cationic micelles catalyze the reaction, while anionic micelles inhibit the reaction .…”

mentioning

confidence: 99%

“…The hydrolysis of phosphorus acid esters has been studied in detail in aqueous and single micellar solutions. [51][52][53][54][55][56] The reaction proceeds through breaking the P-O bond, which is facilitated by the presence of electron-withdrawing groups. Cationic micelles catalyze the reaction, while anionic micelles inhibit the reaction.…”

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confidence: 99%

Nanosized Reactors Based on Polyethyleneimines: From Microheterogeneous Systems to Immobilized Catalysts

et al. 2007

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Effective nanoreactors based on polyethyleneimines (PEIs) for the hydrolytic cleavage of O-alkyl O-p-nitrophenyl chloromethylphosphonates (alkyl = ethyl, hexyl) and di(p-nitrophenyl)phosphate were developed in conformity with the idea of modeling the polyfunctional catalytic mechanism of enzymes. A step-by-step modification of the single PEI solution by additives with their own catalytic activities (sodium dodecyl sulfate and lanthanum salt) gave rise to a marked improvement in the reaction efficiency. A 104-106-fold acceleration of the reaction compared to the aqueous basic hydrolysis of the substrates was achieved in the sodium dodecyl sulfate-polyethyleneimine-La(III) ternary system. This system can be considered to be metallomicelles immobilized on a hydrophilic polymer matrix. When the PEI immobilized on silica gel was used as a catalyst, the full completion of the reaction was achieved for 100 min under mild conditions, while the half-life of the reaction in a comparable homogeneous regime exceeds 100 h.

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“…TBP, a phosphotriester, is chemically hydrolyzed via the intermediates dibutyl and monobutyl phosphate (DBP and MBP, respectively) to butanol (3 mol/mol) and phosphoric acid (1 mol/mol) (4). The pathway of biodegradation would probably be similar (3,5).…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of Tributyl Phosphate by Naturally Occurring Microbial Isolates and Coupling to the Removal of Uranium from Aqueous Solution

Thomas

Macaskie

1996

Environ. Sci. Technol.

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Tributyl phosphate (TBP) is widely used as a solvent and plasticizer with a special use as a solvent for the extraction of uranium and plutonium from other radionuclides in nuclear fuel reprocessing. Although the biodegradation of alkyl phosphates by microorganisms has been noted in the literature, biodegradation of TBP is little-documented. The proposed products of the degradation are potentially useful; the liberated 1-butanol as a biomass growth substrate and the co-released inorganic phosphate moiety as a ligand that can precipitate with heavy metals to retain these as biominerals on the biomass. Microorganisms growing on TBP were isolated from industrially contaminated sites and from laboratory enrichment cultures. A mixed culture, containing Pseudomonas spp., supported the deposition of heavy metal (uranyl) phosphate and the removal of the latter from solution (biodecontamination). This general biocatalytic approach has been reported previously; these new isolates show potential for the simultaneous treatment of two classes of waste: the breakdown of one waste (TBP) could be harnessed to the treatment of another class of waste (heavy metals) This approach would represent a considerable advance over established bioprocesses for metal removal, where the cost of the addition of exogenous organophosphate substrate (phosphate donor for the metal precipitation reaction) may ultimately limit their use.

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Kinetics of the Hydrolysis of Phosphate Esters

Cited by 34 publications

References 68 publications

Orientation and Specific Interactions of Nucleotides and Nucleolipids Inside Monoolein-Based Liquid Crystals

Orientation and Specific Interactions of Nucleotides and Nucleolipids Inside Monoolein-Based Liquid Crystals

Nanosized Reactors Based on Polyethyleneimines: From Microheterogeneous Systems to Immobilized Catalysts

Biodegradation of Tributyl Phosphate by Naturally Occurring Microbial Isolates and Coupling to the Removal of Uranium from Aqueous Solution

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