Isolation and Characterization of Actinoramides A-C, Highly Modified Peptides from a Marine Streptomyces sp

Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey’s and Mosher’s methods.