| Abstract: | (2S,3S)‐2‐Amino‐3‐hydroxy‐5‐(4‐nitrophenoxy)pentanoic acid ( 5 ) was prepared stereoselectively as the N‐Fmoc, O‐(tert‐butyl)‐protected derivative 5a in eleven steps from ethyl (E)‐4‐benzyloxypent‐2‐enoate ( 6 ). This protected amino acid was used for the solid‐phase peptide synthesis of oligopeptides, which serve as sequence‐specific chromogenic protease substrates when used in the presence of NaIO4 and bovine serum albumin. The peptide 1 (KRAVNle? 5 ? EANleNH2 (Nle=norleucine)) allows detection of HIV‐protease activity spectrophotometrically at 405 nm. |
