Synthesis of all the stereoisomers of statine (4-amino-3-hydroxy-6-methylheptanoic acid). Inhibition of pepsin activity by N-carbobenzoxy-L-valyl-L-valyl-statine derived from the four stereoisomers

Abstract

Synthesis of all 4 stereoisomers of the novel amino acid statine, 4-amino-3-hydroxy-6-methylheptanoic acid, found in pepstatin [a peptide antibiotic], a potent acid protease inhibitor, was accomplished. Carbobenzoxy-L-valyl-L-valyl-statine tripeptides derived from all 4 stereoisomers were prepared and their effect on pepsin activity was compared to that of pepstatin.