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Bis‐Coenzyme Q 0 : Synthesis, Characteristics, and Application
Author(s) -
Wang Xiuwen,
Ma Wei,
Ying Yilun,
Liang Jie,
Long YiTao
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000477
Subject(s) - chemistry , redox , electron paramagnetic resonance , electrochemistry , intramolecular force , electron transfer , benzoquinone , cyclic voltammetry , coenzyme q – cytochrome c reductase , methylene , hydrogen bond , diamagnetism , photochemistry , medicinal chemistry , molecule , stereochemistry , inorganic chemistry , organic chemistry , electrode , nuclear magnetic resonance , physics , mitochondrion , cytochrome c , biochemistry , quantum mechanics , magnetic field
A methylene‐bridged bis‐coenzyme Q 0 , bis(2,3‐dimethoxy‐5‐methyl‐l,4‐benzoquinone)methane (Bis‐CoQ 0 ), that shows intramolecular electronic communications has been synthesized for the first time. By employing electrochemical, in situ UV/Vis, and electron paramagnetic resonance (EPR) spectroelectrochemical techniques, the unstable reduced intermediate species—monoradicals, diamagnetic dianions and tetraanions of Bis‐CoQ 0 —have been observed. The electron‐transfer process can be defined as a three‐step reduction process with a total of four electrons in solution in CH 3 CN. The chemical reaction in the third redox step process was confirmed by variable temperature cyclic voltammetry. In an aprotic CH 3 CN solution, the peak potential separation between electron‐transfer steps diminished sequentially with increasing concentration of water. The hydrogen‐bonding interactions between water and the electrochemically reduced intermediates of Bis‐CoQ 0 can be estimated by peak potential shifts. The electronic communications of Bis‐CoQ 0 may have been blocked when one reduction peak was observed with proper quantities of water in CH 3 CN solution. The antioxidant defense capacity of Bis‐CoQ 0 ‐protected cells has also been assessed.