Fragmentation of β-hydroxy hydroperoxides.

Xiaodong Gu, Wujuan Zhang, Robert G Salomon

Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.

The Journal of organic chemistry 2012 Feb 3

filter terms:

A β-hydroxy hydroperoxide was obtained through base-catalyzed disproportionation of a hydroperoxy endoperoxide available by singlet oxygenation of cyclohepta-1,4-diene. Vitamins E and C induce fragmentation of this β-hydroxy hydroperoxide generating aldehydes, especially in the presence of redox active metal ions such as those present in vivo, e.g., under conditions of "iron overload". This chemistry may contribute to the oxidative cleavage of polyunsaturated fatty acyls that produces similar aldehydes, which damage proteins and DNA through covalent adduction resulting in "oxidative injury".