Reinvestigation of Alloxantin and Dialuric Acid

Tipson, R. Stuart; Cretcher, Leonard H.

doi:10.1021/jo50001a011

Cited by 23 publications

(7 citation statements)

References 14 publications

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“…The product, dialuric acid monohydrate, was obtained by recrystallization from boiled, deoxygenated water. Dialuric acid gave an IR spectrum, elemental analysis, and X-ray diffraction patterns consistent with those in the literature (9).…”

Section: Methodssupporting

confidence: 85%

“…Dialuric acid monohydrate was prepared following literature procedures. It gave a satisfactory elemental analysis and its IR spectrum and X-ray powder pattern were identical to the published data (9). Heating at 76 or LOO' led to the formation of the anhydrous form.…”

Section: Resultssupporting

confidence: 73%

“…Dialuric acid was prepared according to a previous method (9). Two grams of recrystallized alloxan5 was dissolved in 100 ml of freshly boiled deoxygenated water.…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

The Desolvation and Oxidation of Crystals of Dialuric Acid Monohydrate

Clay

Knevel

Byrnx

1982

Journal of Pharmaceutical Sciences

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Section: Methodssupporting

confidence: 85%

Section: Resultssupporting

confidence: 73%

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The Desolvation and Oxidation of Crystals of Dialuric Acid Monohydrate

Clay

Knevel

Byrnx

1982

Journal of Pharmaceutical Sciences

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“…Crystal data show that dialuric acid exists in the dihydroxydioxo form ( IV ), but 1 H‐NMR studies of dimethyl sulfoxide (DMSO) solutions suggest the existence of a monohydroxytrioxo structure ( I ). However, on the basis of its infrared spectrum, it was concluded that dialuric acid exists in the trioxo form, a conclusion considered doubtful . In view of the small difference in their energies, our theoretical calculations predict that both I and IV coexist.…”

Section: Resultsmentioning

confidence: 99%

Theoretical investigation of the alloxan-dialuric acid redox cycle

Kakkar

Bhandari

2013

Int. J. Quantum Chem

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The redox cycle between alloxan, a mild oxidizing agent, and its reduction partner, dialuric acid, is investigated using density functional theory. It is found that the initial step is the one‐electron reduction of alloxan followed by protonation, yielding a stable neutral radical, AH·. The radical can then accept another electron to form the dialuric acid anion. The formation of this anion is thermodynamically favored in both the gas phase and in solution. The radical may also undergo dimerization to alloxantin, followed by the transfer of a proton from one moiety to another, yielding alloxan and dialuric acid. This reduction is thermodynamically feasible in the gas phase, but not in aqueous solution. In the case of reduction of alloxan by glutathione at the physiological pH, computed redox potentials indicate that a two‐electron reduction is the favored course of reaction, yielding directly the dialuric acid anion, which then undergoes aerial oxidation to yield the superoxide radical. The redox cycling between alloxan and dialuric acid is responsible for the diabetogenic activity of alloxan, producing cytotoxic radicals on reoxidation of dialuric acid. © 2013 Wiley Periodicals, Inc.

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“…The HB was prepared by adopting the procedure by Tipson and Cretcher [14]. The product was recrystallized in hot water and characterized by spectral analysis.…”

Section: Exferimjy?tmmentioning

confidence: 99%

On the electrochemical oxidation of 5‐hydroxy barbituric acid

Berchmans

Vijayavalli

1994

Electroanalysis

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The electrochemical behavior of 5-hydro? barbituric acid (HB) has been investigated in aqueous and nonaqueous media. In aqueous medium, there is only one anodic peak at -50 my (at 21 = 20 mV/s), and no cathodic peak is observed indicating an irreversible reaction under the conditions of this studyThe cyclic voltammograms indicate a two-electron transfer reaction corresponding to the oxidation of HB to alloxan monohydrate (AM). In nonaqueous medium, voltammetric response is observed both in the anodic as well as the cathodic directions. The anodic peak occurs at +140 mV and the cathodic peak occurs at -320 mV at c = 20 mV/s. At high scan rates (u > 200 mV/s) there are m o cathodic peaks. The mechanism of oxidation of HB is discussed. and the rate constants of the reaction are calculated.

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Reinvestigation of Alloxantin and Dialuric Acid

Cited by 23 publications

References 14 publications

The Desolvation and Oxidation of Crystals of Dialuric Acid Monohydrate

The Desolvation and Oxidation of Crystals of Dialuric Acid Monohydrate

Theoretical investigation of the alloxan-dialuric acid redox cycle

On the electrochemical oxidation of 5‐hydroxy barbituric acid

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