C. Turck, H. Berndt
Jun 1, 1981
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Journal
Hoppe-Seyler's Zeitschrift fur physiologische Chemie
Abstract
Reacting 3-(N alpha-Benzyloxycarbonylalanyl-phenylalanyloxy)-2-hydroxy-N-methylbenzamide with glycinediethylamide at temperatures within 60-100 degrees C, utilizing either dimethylsulfoxide, dimethylformamide or N-methylpyrrolidone as solvents, yielded the corresponding tripeptide derivative Z-Ala-D/L-Phe-Gly-N(Et)2. Depending on the reaction temperature and the nature of the solvent, the isolated tripeptide derivatives contained 0.55% (60 degrees C, dimethylformamide) to 2.5% (100 degrees C, dimethylformamide) of the D-epimer, which could be separated by high-performance liquid chromatography. 3-(N alpha-Benzyloxycarbonylpeptidyloxy)-2-hydroxy-N-methylbenzamide derivatives allow peptide couplings at elevated temperatures even in those cases where the poor solubility of the amino components prevents the condensation step with those methods operating at low temperatures.