Abstract
Peptidep-nitroanilides (peptidepNAs) have found wide application as chromogenic substrates. An improved SPPS method to synthesize rapidly and in good yield a broad range of peptidepNAs under mild conditions will be presented here. To obtain a suitable carrier, the (4-aminophenyl)aminocarbonyloxy derivatives of Wang resin and Sasrin were synthesized. SPPS employing Fmoc/tBu-based protection followed by acidolytic cleavage yielded the (protected) peptidep-aminoanilide which was oxidized with sodium perborate in acetic acid to yield the (protected) peptidepNA. Side-chain protection proved to be advantageous. Acid-labile peptidepNAs such as the proteasome substrate Z-Glu(OtBu)-Ala-Leu-pNA thus can be obtained directly. The behavior of Cys, Met, Tyr and Trp being susceptible towards oxidation was studied more closely.
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