pseudomycin-a and Mycoses

The gamma hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C' provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical synthesis of a minor fermentation factor pseudomycin C' and related analogues is reported.

Topics: Acylation; Animals; Antifungal Agents; Aspergillus fumigatus; Candida; Cryptococcus neoformans; Histoplasma; Mice; Microbial Sensitivity Tests; Models, Animal; Mycoses; Parasitic Sensitivity Tests; Peptides, Cyclic; Structure-Activity Relationship; Survival Rate