10.1016/S0040-4020(01)97645-8
The research presents an in-depth investigation into the biosynthesis of flexirubin, a pigment produced by the gliding bacterium Flexibacter elegans. The study aimed to trace the origin of the benzene ring B and its substituents in flexirubin, using "C- and "C-labeled acetate and butyrate. The conclusions drawn from the experiments were that all carbon atoms of ring B and its alkyl substituents are derived from acetate, with 3-dodecylorsellinic and orsellinic acid identified as intermediates in the biosynthesis. The research also established that the carboxyl group of orsellinic acid is lost before the ester linkage with the w-phenyl-polyene carboxylic acid or its precursor is formed. Chemicals used in the process included various isotopically labeled precursors such as [1-14C]acetate, [2-14C]acetate, [1-14C]butyrate, and [1-13C]propionate, as well as reagents for chemical degradation and analysis like lithium aluminum hydride, ozone, and p-bromo-phenacyl bromide. The study employed techniques such as mass spectrometry, NMR spectroscopy, and high-performance liquid chromatography to analyze the distribution of radioactivity and isotopic enrichment in the synthesized flexirubin and its degradation products.