67025-06-3Relevant academic research and scientific papers
Synthesis and spectroscopic characterization of [5-13C]- and [6-13C]ubiquinone-10 for studies of bacterial photosynthetic reaction centers
Boers, Rutger B.,Gast, Peter,Hoff, Arnold J.,De Groot, Huub J. M.,Lugtenburg, Johan
, p. 189 - 202 (2007/10/03)
This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-13C]- and [3-13C]ubiquinone-0 and of [5-13C]- and [6-13C]ubiquinone-10. A scheme based on the synthetic approach to [5-13C]ubiquinone-10 has been worked out for the synthesis of ubiquinones 13C-labeled at any individual position and at every combination of positions in the quinone ring. The [5-13C]- and [6-13C]ubiquinone-10 isotopomers were incorporated into the QA-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of QA with a dynamic perturbation involving the 4-carbonyl functionality.
Synthesis and spectroscopic characterization of [1′-14C]ubiquinone-2, [1′-14C]-5-demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-demethoxyubiquinone-2
Van Der Klei, Anita,De Jong, Robertus L. P.,Lugtenburg, Johan,Tielens, Aloysius G. M.
, p. 3015 - 3023 (2007/10/03)
[1′-14C]Ubiquinone-2, [1′-14C]-5-demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-demethoxyubiquinone-2 have been synthesised from [1-14C]acetic acid. A common feature of these benzoquinones is the isoprenoid chain, and the 14C-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, 1H NMR and 13C NMR.
Synthesis of optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone
Miyaoka, Hiroaki,Kajiwara, Yasuhiro,Hara, Miho,Suma, Akira,Yamada, Yasuji
, p. 3189 - 3196 (2007/10/03)
Optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone and 6-acetoxymethyl-3-alkoxy-6-methyl-2-cyclohexenone were efficiently obtained by lipase-catalyzed kinetic resolution. (R)-6-Acetoxymethyl-3-(methoxymethoxy)-6-methyl-2-cyclohexenone was converted to the synthetic intermediate of cassiol.
