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Synthesis and Spectroscopic Characterization of [1′‐ 14 C]Ubiquinone‐2, [1′‐ 14 C]‐5‐Demethoxy‐5‐hydroxyubiquinone‐2, and [1′‐ 14 C]‐5‐Demethoxyubiquinone‐2
Author(s) -
van der Klei Anita,
de Jong Robertus L. P.,
Lugtenburg Johan,
Tielens Aloysius G. M.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:17<3015::aid-ejoc3015>3.0.co;2-g
Subject(s) - chemistry , quinone , terpenoid , stereochemistry , mass spectrometry , acetic acid , organic chemistry , chromatography
[1′‐ 14 C]Ubiquinone‐2, [1′‐ 14 C]‐5‐demethoxy‐5‐hydroxyubiquinone‐2, and [1′‐ 14 C]‐5‐demethoxyubiquinone‐2 have been synthesised from [1‐ 14 C]acetic acid. A common feature of these benzoquinones is the isoprenoid chain, and the 14 C‐label has therefore been incorporated in this isoprenoid. The coupling of the different quinone head groups and the isoprenoid chain is the last step in the total synthesis, to prevent unnecessary loss of the labelled material during synthesis. The products have been characterised by mass spectrometry, 1 H NMR and 13 C NMR.