Biosynthesis of gliotoxin and mycelianamide.

Mycelium of Penicillium terlikowski was permeable to both L-[carboxyl-14C]phenylalanine and cyclo L-[carbonyl-14C]phenylalanyl-L-seryl. The former compound was incorporated well and the latter poorly into gliotoxin produced by stationary cultures of the organism. Mycelium of Penicillium patulum was permeablt to L-[CARBONYL-14C]tyrosyl and cyclo L-alanyl-d-[carbonyl-14C]tyrosyl. These cyclic depeptides were not incorporated into mycelianamide produced by stationary cultures of the organism, but both1carboxyl-14C]tyrosine were incorporated. The latter was incorporated in a specific manner into part of the mycelianamide molecule. The results did not support the postulate that the appropriate cyclic dipeptides, as outlined above, were free intermediates in the biosynthesis of gliotoxin or mycelianamide.