BENZYLOXYCARBONYLARGININE NITROPHENYL ESTER SALTS: 1‐HYDROXYBENZOTRIAZOLE CATALYZED ACYLATIONS OF AMINES

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Abstract
Benzyloxycarbonylarginine p-nitrophenyl ester was prepared by the p-nitrophenyltrifluoroacetate method. The p-nitrophenyl ester derivative was isolated as its crystalline picrate and nitrate salts. The ester salts couple with amino compounds in the presence of 1-hydroxybenzotriazole, but decompose without acylation of amines in the absence of the 1-hydroxybenzotriazole catalyst. Benzyloxycarbonylarginine p-nitrophenyl ester and other activated esters of N-.alpha.-substituted arginine salts may be useful reagents for introduction of trypsin-labile protecting groups into peptide fragments for purpose of polypeptide semi-synthesis. Side reactions of such carboxyl-activated arginine derivatives may serve as models for side reactions in the couplings of peptide fragments with arginine residues in the carboxyl-terminal position. Peptide fragment couplings of this type may frequently be encountered in semi-synthesis of polypeptides from tryptic fragments.