Synthesis of peptides analogous to the N-terminal eicosapeptide sequence of ribonuclease A. Part I. Synthesis of the orn10-hexapeptide analogue of the sequence 7–12

Abstract

Synthesis is described of the protected hexapeptide N^α-benzyloxycarbonyl-N^ε-t-butoxycarbonyl-L-lysyl-L-phenylalanyl-γ-t-butyl-L-glutamyl-N^δ-t-butoxycarbonyl-L-ornithyl-L-glutaminyl-L-histidine methyl ester, analogous to positions 7–12 in the amino-acid sequence of bovine pancreatic ribonuclease A.

The synthesis was carried out by coupling, by the azide procedure, the dipeptide N^α-benzyloxycarbonyl-N^ε-t-butoxycarbonyl-L-lysyl-L-phenylalanine hydrazide with γ-t-butyl-L-glutamyl-N^δ-t-butoxycarbonyl-L-ornithyl-L-glutaminyl-L-histidine methyl ester.