Verfahren zur Herstellung argininhaltiger Peptiden

摘要

1311103 Arginine-containing peptides FARBWERKE HOECHST AG 14 May 1970 [14 May 1969] 23474/70 Heading C2C Novel arginine-containing peptides wherein the guanidino group is protected by two adamantyloxycarbonyl groups are prepared by reacting (1) X-Arg(AdOC) 2 -OH with the amino group of an amino acid or peptide or (2) H-Arg(AdOC) 2 -Y with the carboxyl group of an amino acid or peptide (X is a protecting group, or an aminoacid or peptide radical and Y is OH, a protecting group or an amino acid or peptide radical). Arginine in which the guanidino group is similarly protected by two adamantyloxy-carbonyl groups is also claimed per se. The novel compounds X-Arg(AdOC) 2 -OH and H-Arg(AdOC) 2 -Y may be prepared by reacting X-Arg-OH or H-Arg-Y with adamantyloxycarbonyl chloride. Intermediates isolated are Z-gln-ala-OBut; Z - pro - gln - ala - OBut; Z - asn - pro - glnala - OBut;Z - gln - asn - pro - glu - ala - OBut; ala - OBut; Z - gln-asn-proglu - ala - OBut; BOC - ala - gln - asn - pro - gln - ala - OBut; H or Z-glu(OBut)-ala-gln-asn-pro-gln-ala-OH; H or Z - pro - val - lys(BOC) - val - tyr - NH 2 and AdOC-OSn (OSn = N-hydroxy-succinimide ester group). The adamantyloxycarbonyl group may be cleaved to form the desired peptide by use of an organic or inorganic acid, e.g. CF 3 COOH.