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Coenzyme Q


DATA No : VCQ0019 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-5-methyl-6-pentyl-1,4-benzoquinone

COMMON NAME: 6-Pentyl coenzyme Q
SYMBOL: PB
FORMULA: C18H28O4 MOL.WT (average) : 308.413


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BIOLOGICAL ACTIVITY
The reoxidation phase of the catalytic cycle of succinate dehydrogenase was studied in Complex II preparations by the rapid freeze-electron paramagnetic resonance (epr) technique. 2,3-Dimethoxy-5-methyl-6-pentyl-1,4-benzoquinone<0019> , as the oxidant, the observed reoxidation of the epr-detectable components, previously reduced with dithionite or succinate, came to completion within a few milliseconds well within the turnover time of the enzyme.(Ref. 0041)
PHYSICAL AND CHEMICAL PROPERTIES
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SPECTRAL DATA
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NMR SPECTRA:methoxyyl hydrogens; d 4.0 ppm (S), methyl group which is bonded to the ring carbon atom ; d 2.0 ppm . Solvent; CDCl3. Internal standard; TMS. (Ref. 0040)

MASS SPECTRA:Molecular ion; m/e 252, tropylium ion; m/e 197, monomethoxyl tropylium ion, m/e 167 (Ref. 0040)

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CHEMICAL SYNTHESIS
To a solution of 2,3-dimethoxy-5-methyl-1,4-benzoquonone in acetic acid was added, in portions, the diacyl peroxide with stirring at 90 - 95deg C for 1 - 2 hours under nitrogen. The reaction mixture was heated another 10 - 20 hours. The solution was concentrated, in vacuo, to dryness and residue was subjected to silica gel column chromatography. The collected orange fraction was further purified on preparative thin layer plates to give a pure product. (Ref. 0040)
METABOLISM

GENETIC INFORMATION

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REFERENCES
[0040]
AUTHOR:Wan, Y. P., Williams, R. H., Folkers, K., Leung, K. H., and Racker, E.
TITLE:Low molecular weight analogs of coenzyme Q as hydrogen acceptors and donors in systems of the respiratory chain PubMed ID:1125004
JOURNAL:Biochem Biophys Res Commun.
VOL:63 PAGE : 11-15 (1975)
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[0041]
AUTHOR:Ackrell, B. A., Kearney, E. B., Coles, C. J., Singer, T. P., Beinert, H., Wan, Y. P., and Folkers, K.
TITLE:Kinetics of the reoxidation of succinate dehydrogenase PubMed ID:196550
JOURNAL:Arch Biochem Biophys.
VOL:182 PAGE : 107-117 (1977)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.