Kinetics of Oxidative Deamination and Decarboxylation of L-Asparagine by Alkaline Permanganate: a Mechanistic Approach

Kembhavi, M.D. Saleem R.; Harihar, Abdulazizkhan L.; Nandibewoor, Sharanappa T.

doi:10.1515/irm-2001-0105

Cited by 4 publications

(2 citation statements)

References 12 publications

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“…Microbiologically mediated degradation of EDTA in circumneutral pHs also proceeds via the formation of ED3A, N,N′-ethylenediaminediacetic acid (EDDA), iminodiacetatic acid (IDA), and low-molecularweight compounds (9,10). Experiments with model compounds such as amino acids (e.g., [11][12][13][14] have shown that the reduction of permanganate by these species at high pHs proceeds via formation of manganate MnO4 2-, hypomanganate MnO4 3-(15), and finally MnO2 or mixed Mn(III)/Mn-(IV) solids (16). Identified reaction products formed upon the permanganate oxidation of amino acids and other model compounds include ammonia, oxalate, CO2, and traces of aldehydes (17)(18)(19)(20).…”

Section: Introductionmentioning

confidence: 99%

Investigation of Mechanisms of Oxidation of EDTA and NTA by Permanganate at High pH

Chang

Korshin

Ferguson

2006

Environ. Sci. Technol.

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Permanganate has been used for oxidation of nuclear wastes containing chelating agents such as ethylenediaminetetraacetic and nitrilotriacetic acids (EDTA and NTA) to improve separation of radionuclides and heavy metals from the wastes, butthe mechanisms of degradation of these and related organic ligands at high pHs have not been studied. EDTA, NTA, and the model compound ethylenediamine (EN) were found to be readily oxidized by permanganate at pH 12-14. The reduction of permangante was accompanied by formation of unstable manganate and dispersed MnO2 particles, which constituted the final product of permanganate reduction. The yields and speciation of EDTA, NTA, and EN breakdown products were affected by the pH and permanganate dose. Iminodiacetic acid (IDA), oxalate, formate, and ammonia were the predominant EDTA and NTA oxidation products. Mineralization of EDTA, NTA, and EN to CO2 was more significant at pH 12. At pH 14 formation of oxalate and deamination to NH3 were the most important reactions. IDA was released upon the oxidation of both EDTA and NTA, but EDTA oxidation yielded no ethylenediaminediacetic acid (EDDA). The speciation of the reaction products indicated that the ethylene group in EDTA was the preferred attack site in oxidations by alkaline permanganate.

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Section: Introductionmentioning

confidence: 99%

Investigation of Mechanisms of Oxidation of EDTA and NTA by Permanganate at High pH

Chang

Korshin

Ferguson

2006

Environ. Sci. Technol.

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“…Many investigators [8][9][10][11][12][13][14][15][16][17] have suggested that most of the oxidation reactions by permanganate ion in neutral and alkaline media proceed through intermediate complex formation between the oxidant and substrate. Spectroscopic evidence for such a complex was obtained from the UV-Vis spectra, Fig.…”

Section: Discussionmentioning

confidence: 99%

Base-Catalyzed Oxidation of Aminotriazole Derivative by Permanganate Ion in Aqueous Alkaline Medium: A Kinetic Study

Fawzy¹

2015

IJIRSET

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Kinetic investigation on the oxidation of one of the aminotriazole derivatives, namely N,N-dimethyl-N'-(4H-1,2,4-triazol-3-yl) formamidine (ATF) by permanganate ion in alkaline medium has been performed at a constant ionic strength of 0.1 mol dm -3 and at 25 o C. The progress of the reaction was followed spectrophotometrically. Both spectroscopic and kinetic evidences reveal formation of a 1:1 intermediate complex between the oxidant and substrate. The influence of pH on the oxidation rate indicated that the reaction is base-catalyzed. The reaction shows first order dependence with respect to , and fractional-first order dependences on both [ATF] and [OH -]. Increasing ionic strength and dielectric constant did not affect the reaction rate. Addition of small amounts of alkali-metal ion catalysts was found to accelerate the oxidation rate and the order of effectiveness of the ions was: Li + > Na + > K + . The final oxidation products of ATF were identified as 3-aminotriazole, dimethyl amine and carbon dioxide. A plausible reaction mechanism consistent with the kinetic observations is proposed, and the reaction constants involved in the different steps of the mechanism have been evaluated. The activation parameters with respect to the slow step of the reaction, along with thermodynamic quantities of the equilibrium constants are calculated and discussed.

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The Kinetics of the Oxidation of Lysine by μ-Peroxo-Bridged Binuclear Cobalt (III) Complex of Succinimide in Aqueous Hydrochloric Acid Medium

Adetoro

Idris

Onu

et al. 2017

Annals of Science and Technology

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Kinetics of oxidation of Lysine (Lys) and mechanisms by μ-peroxo bis[bis(ethylenediamine)succinimidato-dicobalt(III)]dinitratedihydrate; [LCo(μ-O2)CoL](NO3)2.2H2O (L = suc(en)2), hereafter the complex, was investigated at 420 nm wavelength of maximum absorption of the complex under the conditions hydrogen ions concentration = 1.8 × 10-2 mol dm-3, temperature = 24 ± 1 °C, [LCo(μ-O2)CoL2+] = 1.4 × 10-4 mol dm-3 and ionic strength = 0.5 mol dm-3. First order in [LCo(μ- O2)CoL2+] and [Lys] were obtained but inverse first order in [H+]. The proposed overall rate equation is as shown: Rate of the reaction decreases when hydrogen ions concentration increase and exhibited converse effect with increase in concentration of ionic strength from 0.1 - 1.3 mol dm-3. Added cations and anions affected the reaction rate and the Michaelis-Menten plot passed through the origin indicating no absence of intermediate complex in the electron transfer processes. Putting all the results obtained together, the most probable reaction mechanism is in favour of outer-sphere and an appropriate rate law is established using steady state approximation.

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Kinetics of Oxidative Deamination and Decarboxylation of L-Asparagine by Alkaline Permanganate: a Mechanistic Approach

Cited by 4 publications

References 12 publications

Investigation of Mechanisms of Oxidation of EDTA and NTA by Permanganate at High pH

Investigation of Mechanisms of Oxidation of EDTA and NTA by Permanganate at High pH

Base-Catalyzed Oxidation of Aminotriazole Derivative by Permanganate Ion in Aqueous Alkaline Medium: A Kinetic Study

The Kinetics of the Oxidation of Lysine by μ-Peroxo-Bridged Binuclear Cobalt (III) Complex of Succinimide in Aqueous Hydrochloric Acid Medium

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