Biosynthesis of Gliotoxin and Mycelianamide

Abstract

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 permeable to L-[carboxyl-14C]tyrosine and to the cyclic dipeptides cyclo L-alanyl-L-[carbonyl-14C]tyrosyl and cyclo L-alanyl-D-[carbonyl-14C]tyrosyl. These cyclic dipeptides were not incorporated into mycelianamide produced by stationary cultures of the organism, but both D- and L-[carboxyl-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.