Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 5, Pages 1058-1063Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b922673g
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Funding
- National Natural Science Foundation of China [20972063, 20621091]
- 111 Project
- Program for New Century Excellent Talents in University [NCET-06-0906]
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alpha-Pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) is a unique enediol antioxidant. To explore the detailed antioxidant mechanism of alpha-pyridoin, we synthesized alpha-pyridoin and its 5,5'- or 6,6'-bis-substituted derivatives (2-7) and compared their capacities to scavenge galvinoxyl radical (GO(center dot)) and protect human red blood cells (RBCs) from oxidative haemolysis. It was found that the compounds (5 and 6) with a methyl or methoxy group at the 5-position exhibit significantly higher GO(center dot)-scavenging and anti-haemolysis activities than other derivatives and vitamin C. Kinetic analysis of the GO(center dot)-scavenging reaction and the effect of added base on the reaction rate revealed that in ethyl acetate, the reaction occurs primarily by the direct hydrogen atom transfer (HAT mechanism). However, in ethanol that supports ionization, the kinetics of the process is mostly governed by sequential proton loss electron transfer (SPLET mechanism).
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