Artificially elicited capabilities of enzymes and their application in natural product chemistry

Abstract

By exploiting the stereospecificity of farnesyl diphosphate synthase reaction, both the S and R isomers of E, E-4-methylfarnesol and their derivatives, including faranal, 4-MeJH I, and their congeners were synthesized from E- (1) and Z.-3-methyl-3-pentenyl diphosphate (2), respectively. Compound 1 acted as substrate in the reaction with various allylic diphosphate substrates catalyzed by undecaprenyl diphosphate synthase of Bacillus subtilis giving enantiomerically pure products. The reaction, however, stopped at the stage of a single condensation, thereby forming S-enantiomers of 2-Z-methylprenyl derivatives Both 1 and 2 were accepted by nonaprenyl diphosphate synthase obtained from Micrococcus luteus condensing with allylic substrates to give S- and R-enantiomers of various polyprenyl derivatives, respectively. © 1989 IUPAC