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- W18689654 abstract "5-Phenyl-4-pentenyl-hydroperoxide (PPHP) has been synthesized as a mechanistic probe for the reactions of hydroperoxides with metals and metalloproteins. Oxidation of PPHP by di-t-butyl-peroxyoxalate generated peroxyl radical cyclization products in 60% isolated yield. Reduction of PPHP by Fe/sup 2 +/-cysteine produced alkoxyl radical cyclization products in 40% yield along with 24% of 5-phenyl-4-pentenyl-alcohol (PPA). Reaction of PPHP with hematin produced 5-phenyl-4-pentenal (PPAL) in 96% yield. The structures of all products were assigned by high resolution NMR and mass spectroscopy and confirmed by independent synthesis. The fact that PPHP was converted by one-electron oxidation, one-electron reduction, and two-electron reduction to unique products prompted its use as a probe of metalloprotein- peroxide interactions. Horseradish peroxidase catalyzed the quantitative reduction of PPHP to PPa by phenol. Quantitative reduction in the presence of phenol was also catalyzed by catalase, lactoperoxidase, cytochrome c peroxidase, and prostaglandin H synthase. In contrast, microperoxidase, metmyoglobin, and methemoglobin catalyzed the conversion of PPHP to PPAL (80%) and PPA (20%) in either the presence or absence of phenol. The latter proteins exhibited low turnover numbers relative to the classical peroxidases. The results indicate that the PPHP can be used to differentiate a wide range of hemeproteins that reduce hydroperoxides by onemore » or two electrons. Furthermore, the spectrum of products derived from it provides important information about the pathways of its metabolism.« less" @default.
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- W18689654 date "1986-05-01" @default.
- W18689654 modified "2023-09-24" @default.
- W18689654 title "5-Phenyl-4-pentenyl-hydroperoxide: a probe for hydroperoxide - metalloprotein interactions" @default.
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