Université de Fribourg

Mechanistic aspects of alloxan diabetogenic activity: a key role of keto-enol inversion of dialuric acid on ionization

Czerwiñska, Małgorzata ; Sikora, Adam ; Szajerski, Piotr ; Adamus, Jan ; Marcinek, Andrzej ; Gębicki, Jerzy ; Bednarek, Paweł

In: The Journal of Physical Chemistry A, 2006, vol. 110, no. 22, p. 7272 -7278

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...