Synthesis and stability of [3H] 5—demethoxyubiquinone-9

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Abstract

Radioactive [3H]5-demethoxyubiquinone-9 (3-methyl-2-nonaprenyl-6-methoxy-1,4-benzo-quione), an intermediate in the biosynthesis of ubiquione-9 by selected microorganisms and by the rat, has been synthesized. 4-Methyl-3-nitrophenol was converted to the corresponding anisole with [3H]methyl iodide and the anisole was then reduced to the corresponding aniline. Oxidation of 6-methyl-3-methoxy [3H]aniline with chromic acid gave the corresponding 1,4-benzo-quinone which was reduced and alkylated with solanesol in the presence of boron trifluorideetherate. Oxidation with ferric chloride gave two isomers, 5-demethoxyubiquinone-9 and 6-methyl-2-nonaprenyl-3-methoxy-1,4-benzoquinone which were separated by thin layer chromatography. The [3H]methoxyl-5-demethoxyubiquinone-9 prepared had a specific radioactivity of 100 mCi/mmole.

References (17)

  • S. Imamoto et al.

    Tetrahedron Letters

    (1967)
  • B.C. Das et al.

    Biochem. Biophys. Res. Commun.

    (1967)
  • E.R. Redfearn et al.

    Biochim. Biophys. Acta

    (1962)
  • P. Friis et al.

    J. Am. Chem. Soc.

    (1966)
  • R.E. Olson et al.
  • B.L. Trumpower et al.
  • B.L. Trumpower et al.

    J. Biol. Chem.

    (1972)
  • W.K. Anslow et al.

    J. Chem. Soc.

    (1938)
There are more references available in the full text version of this article.

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    The mutant mitochondria instead exhibited a major peak eluting 1 min earlier than UQ9 (Fig. 1, C–E). The slightly polar nature and the absorption property (absorption peak at 270 nm, Fig. 2 B) of this compound coincide well with those reported for the ubiquinone biosynthesis intermediate, DMQ9(see Fig. 3) (19, 23). A mass spectrometry analysis of the accumulated quinone in clk-1(qm51) mutant detected a molecular ion peak atm/z 765, which corresponds to the molecular mass of DMQ9 (theoretical mass [C53H80O3] = 765.2005) (Fig.4).

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Part of this report was taken from a dissertation submitted by Bernard L. Trumpower to St. Louis University (1969) in partial fulfillment of the requirement for the Ph.D. degree. Present address: Department of Biochemistry, Dartmouth Medical School, Hanover, New Hampshire, USA.

∗∗

Present address: Department of Chemistry, Presbyterian College, Clinton, South Carolina, USA.

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