Synthesis of 13C-labeled ubiquinone-acetogenin hybrid inhibitors of mitochondrial complex I

Natural acetogenins are the most potent inhibitors of mitochondrial complex I. By synthesizing a ubiquinone-acetogenin hybrid inhibitor (named Q-acetogenin), we previously showed that a γ-lactone ring of acetogenins is completely substitutable with a ubiquinone ring. In this study, to open a new experimental approach to the study of acetogenin-complex I interaction, we report procedures for synthesizing 13C-labeled Q-acetogenins, wherein the carbonyl carbon at the 1- or 4-position of the ubiquinone ring is specifically 13C-labeled.