β-羟过氧化物的碎片化。
Fragmentation of β-hydroxy hydroperoxides.
机构信息
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.
出版信息
J Org Chem. 2012 Feb 3;77(3):1554-9. doi: 10.1021/jo201910g. Epub 2012 Jan 24.
Abstract
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".
摘要
通过基催化分解可得到β-羟基过氧化物，该过氧化物可通过单线态氧氧化环庚-1,4-二烯得到。维生素 E 和 C 诱导该β-羟基过氧化物的断裂，生成醛，特别是在存在氧化还原活性金属离子的情况下，例如，在体内存在的情况下，例如，在“铁过载”的情况下。这种化学可能有助于产生类似醛的多不饱和脂肪酸的氧化断裂，通过共价加合导致蛋白质和 DNA 损伤，从而导致“氧化损伤”。
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