Mechanistic aspects of alloxan diabetogenic activity: a key role of keto-enol inversion of dialuric acid on ionization
- Czerwiñska, Małgorzata Institute of Applied Radiation Chemistry, Technical University of Lodz, Poland
- Sikora, Adam Institute of Applied Radiation Chemistry, Technical University of Lodz, Poland
- Szajerski, Piotr Institute of Applied Radiation Chemistry, Technical University of Lodz, Poland
- Adamus, Jan Institute of Applied Radiation Chemistry, Technical University of Lodz, Poland
- Marcinek, Andrzej Institute of Applied Radiation Chemistry, Technical University of Lodz, Poland
- Gębicki, Jerzy Institute of Applied Radiation Chemistry, Technical University of Lodz, Poland
- Bednarek, Paweł Department of Chemistry, University of Fribourg, Switzerland
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06.04.2006
Published in:
- The Journal of Physical Chemistry A. - 2006, vol. 110, no. 22, p. 7272 -7278
English
The inversion of the keto-enol stability order of dialuric acid on ionization was calculated and verified experimentally. The radical cations in both forms were characterized. The spectrum of the keto form was observed upon direct ionization of dialuric acid under matrix conditions, whereas the enol form was formed upon a sequential electron-proton-proton attachment to alloxan under acidic aqueous condition. Facilitation of the one-electron oxidation of dialuric acid upon its enolization can result in a more effective formation of superoxide radical anion in the process of its auto-oxidation. This process is discussed in reference to the alloxan diabetogenic action. Both neutral keto and enol forms are energetically close, and under favorable conditions, the auto-oxidation of dialuric acid could involve participation of the enol form.
- Faculty
- Faculté des sciences et de médecine
- Department
- Département de Chimie
- Language
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 8553
- DOI 10.1021/jp0614594
- Persistent URL
- https://folia.unifr.ch/unifr/documents/300579
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