Stereochemistry of Hydrogenation of (-)-Dehydrogriseofulvin to (+)-Griseofulvin with a Cell-Free System of Streptomyces cinereocrocatus

抄録

To elucidate the stereochemistry of the hydrogenation of (-)-dehydrogriseofulvin (1a) to (+)-griseofulvin (3a) by Streptomyces cinereocrocatus, we have prepared from the microorganism a cell-free system which can transform 1a to 3a. The hydrogenation activity of the cell-free system increased in the presence of added reduced nicotinamide adenine dinucleotide phosphate (NADPH). The stereochemistry of hydrogenation was determined by 400 MHz proton nuclear magnetic resonance (¹H-NMR) analysis of the products obtained by the enzymatic conversion of (-)-[5'-²H]-dehydrogriseofulvin (1b) and also by the enzymatic conversion of 1a in medium containing deuterium oxide.