[Synthesis of defined peptide derivatives via aminolysis of 3-[N alpha-acylpepidyloxy)-2-hydroxy-N-alkylbenzamides at elevated temperatures, I. Synthesis of the model peptide derivative Z-Ala-Phe-Gly-N(Et)2 (author's transl)].
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.
D001549:Benzamides; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009842:Oligopeptides / Q000138:chemical synthesis*; D012997:Solvents; D013696:Temperature
D001549:Benzamides; D007202:Indicators and Reagents; D009842:Oligopeptides; D012997:Solvents
Synthese definierter Peptid-Derivate durch Aminolyse von 3-(N alpha-acyl-peptidyloxy)-2-hydroxy-N-alkylbenzamiden bei erhöhten Temperaturen, I. Synthses des Modellpeptid-Derivates Z-Ala-Phe-Gly-N(Et)2.