The rate of enzymic hydrolysis of phosphoric esters. 3. Carboxy-substituted phenyl phosphates

Walker, P. G.; King, E. J.

doi:10.1042/bj0470093

Cited by 23 publications

(4 citation statements)

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“…Additional references are found about its activity as a free enzyme. Walker and King reported a value of 0.6 mM for an electrochemical immunoassay procedure developed in solution. K app M values of 0.082 and 0.056 mM are reported for p -nitrophenyl phosphate and p -aminophenyl phosphate, respectively.…”

Section: Resultsmentioning

confidence: 99%

Amperometric Immunosensors Based on Rigid Conducting Immunocomposites

et al. 1997

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Novel polishable immunosensors based on rigid biocomposite materials have been constructed. These biocomposites contain graphite powder, rabbit IgG, and methacrylate or epoxy resins. This material acts as a reservoir for the biological molecules and as a transducer at the same time. In order to study the potential analytical properties of this new type of material, a competitive binding assay was developed to determine the RIgG present in a sample with the aid of goat anti-rabbit IgG labeled with alkaline phosphatase. Using phenyl phosphate as a substrate, the phenol produced by the enzymatic reaction was amperometrically detected at 800 mV (vs Ag/AgC1). The surface of the immunosensor can be regenerated by simply polishing, obtaining fresh immunocomposite ready to be used in a new competitive assay.

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Section: Resultsmentioning

confidence: 99%

Amperometric Immunosensors Based on Rigid Conducting Immunocomposites

et al. 1997

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“…This may be attributed to the basicity of the ω-amine nitrogen. It has been suggested that as the acidity of the substrate increases the K m value decreases, and in this case, the basic amino group of lysine may contribute to such an increase in K m . , …”

Section: Resultsmentioning

confidence: 99%

Phosphate Prodrugs for Amines Utilizing a Fast Intramolecular Hydroxy Amide Lactonization

1996

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A novel phosphate prodrug system for amines, amino acids, peptides, and peptide mimetics, which utilizes a fast hydroxy amide lactonization of a 3-(2‘-hydroxy-4‘,6‘-dimethylphenyl)-3,3-dimethylpropionic amide system, was developed. Prodrugs of five model amine/amino acids, including p-anisidine, GlyOMe, PheOMe, LysOMe, and Asp-α-OMe, were synthesized. The syntheses of these model phosphate prodrugs were accomplished by coupling the amine or the protected amino acids with 3-[2‘-(dibenzylphosphono)oxy-4‘,6‘-dimethylphenyl]-3,3-dimethylpropionic acid using coupling agents such as bis(2-oxo-3-oxazolidinyl)phosphinic chloride and 1-(3-dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, followed by hydrogenolysis. These phosphate prodrugs were evaluated as substrates for the human placental alkaline phosphatase (AP). The structural features of the amine/amino acids attached to the carboxylic acid group of the promoiety were not found to significantly affect the substrate activity for AP, as evidenced by the small variations observed in the Michaelis−Menten parameters (K m and V max) of the phosphate prodrugs. Results obtained from this study suggest that such a phosphate prodrug system may be applied to a variety of structurally diverse amine-containing drugs.

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“…Dealkylations with trimethylsilyl halides takes place under mild conditions, such that they can also be used for the hydrolysis of esters in which instances strong acidic or alkaline treatments cannot be applied, such as in the cases of nitriles, vinyl ethers and acetals [ 57 , 58 , 59 ]. In addition, various enzyme-catalyzed [ 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 ] hydrolyses have also been elaborated, and there are examples for the application of special catalysts and metal ions as well [ 73 , 74 , 75 , 76 , 77 ].…”

Section: Introductionmentioning

confidence: 99%

The Hydrolysis of Phosphinates and Phosphonates: A Review

Harsági

Keglevich

2021

Molecules

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Phosphinic and phosphonic acids are useful intermediates and biologically active compounds which may be prepared from their esters, phosphinates and phosphonates, respectively, by hydrolysis or dealkylation. The hydrolysis may take place both under acidic and basic conditions, but the C-O bond may also be cleaved by trimethylsilyl halides. The hydrolysis of P-esters is a challenging task because, in most cases, the optimized reaction conditions have not yet been explored. Despite the importance of the hydrolysis of P-esters, this field has not yet been fully surveyed. In order to fill this gap, examples of acidic and alkaline hydrolysis, as well as the dealkylation of phosphinates and phosphonates, are summarized in this review.

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The rate of enzymic hydrolysis of phosphoric esters. 3. Carboxy-substituted phenyl phosphates

Cited by 23 publications

References 3 publications

Amperometric Immunosensors Based on Rigid Conducting Immunocomposites

Amperometric Immunosensors Based on Rigid Conducting Immunocomposites

Phosphate Prodrugs for Amines Utilizing a Fast Intramolecular Hydroxy Amide Lactonization

The Hydrolysis of Phosphinates and Phosphonates: A Review

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