The biosynthesis of ubiquinone: Synthesis and enzymatic modification of biosynthetic precursors

Article abstract of DOI:10.1016/0040-4039(96)00324-3

The synthesis of key intermediates in the eukaryotic biosynthetic pathway of ubiquinone (Q) and the biotransformation of these materials with yeast (S.cerevisiae) mitochondria are described. The synthesis of Q aromatic precursors 2, 3, and 4 (n = 3 in all cases) relies on the palladium (0) catalyzed coupling of farnesyl tributylstannane with suitably functionalized aryl halides. Preliminary experiments show that incubation of synthetic substrate 3 with mitochondria from yeast containing the 3,4-dihydroxy-5-hexaprenylbenzoate methyltransferase gene (COQ3) and S-[methyl-³H]adenosyl-L-methionine yields radiolabeled 4.