Valistatin (3-Amino-2-Hydroxy-4-Phenylbutanoyl-Valyl-Valine), a New Aminopeptidase M Inhibitor, Produced by Streptomyces sp. SL20209

Valistatin, a new inhibitor of aminopeptidase M(AP-M) was discovered in the culture broth of Streptomyces sp. SL20209 isolated from a soil sample. The inhibitor was purified by extraction with n-butanol and the various column chromatographies, and then isolated as whitish powder. The $^1 H-and ^1 H, ^1 H-COSY$ NMR studies, amino acid analysis, and fragmentation patterns by FAB-MS suggested the presence of one 3-amino-2-hydroxy-4-phenylbutanoic acid and two valine residues in the inhibitor. Thus, the structure of valistatin was determined as 3-amino-2-hydroxy-4-phenylbutanoyl-valyl-valine. Valistatin has the molecular formular $C_20H_31N_3 O_5$ (MW 394), and its $IC_50$ value against hog kidney AP-M was determined to be 3.12 $mu g/ml$.