Takeda Y, Mak V, Chang C C, Chang C J, Floss H G
J Antibiot (Tokyo). 1984 Aug;37(8):868-75. doi: 10.7164/antibiotics.37.868.
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 [1,6-14C]shikimic 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.
抗生素酮霉素由莽草酸经分支酸和预苯酸形成。苯丙氨酸和2',5'-二氢苯丙氨酸不是生物合成的中间体。源自[1,6-¹⁴C]莽草酸的酮霉素降解表明,预苯酸转化为酮霉素时,环的两个对映异位边缘之间存在立体特异性区分,前-S-R边缘产生酮霉素环己烯环的C-2'、C-3'侧。