THE CYCLOHEXANE MOIETY OF RAPAMYCIN IS DERIVED FROM SHIKIMIC ACID IN STREPTOMYCES-HYGROSCOPICUS

Although the addition of shikimic acid to the medium had no effect on the level of production of rapamycin by Streptomyces hygroscopicus, C- 14-shikimic acid was incorporated into rapamycin to a very high degree . C-13-Shikimic acid was successfully prepared from 1-[C-13]-glucose u sing a mutant of Klebsiella pneumoniae, and used to label rapamycin. I t was found that C-13-shikimic acid was incorporated into the cyclohex ane moiety of rapamycin, thereby establishing the shikimic acid pathwa y origin of the seven-carbon starter unit.