1984 Volume 37 Issue 8 Pages 868-875
The antibiotic ketomycin is formed from shikimic acid via chorismic acid and prephenic acid. Phenylalanine and 2', 5'-dihydrophenylalanine are not intermediates in the biosynthesis. Degradation of ketomycin derived from [1, 6-14Clshikimic acid showed that prephenic acid is converted into ketomycin with stereospecific discrimination between the two enantiotopic edges of the ring, the pro-S-R edge giving rise to the C-2', C-3' side of the cyclohexene ring of ketomycin.