Untersuchungen über die Kinetik der Spaltung von Di- und Tripeptiden III. Mitt.: Über die rasche Spaltung von Serinpeptiden in rein wässriger Lösung

  • The kinetic data of the hydrolysis of some serine peptides in diluted hydrochloric acid and in pure water and of the rearrangement of O-glycyl-DL-serine to glycyl-DL-serine were determined. The hydrolysis of glycyl-DL-serine and DL-alanyl-DL-serine proceeds surprisingly rapidly in pure water as compared with the hydrolysis of those peptides in 0.5 N hydrochloric acid as well as the hydrolysis of glycyl-DL-alanine in purely aqueous solution. The O → N migration of the glycyl residue in O-glycyl-DL-serine which probably is an intermediate in the cleavage of glycyl-DL-serine in purely aqueous solution represents a three center reaction in which the nucleophilic attack on the O-peptide and peptide bond, respectively, involves a free basic amino group. The analogy between the serine peptide interconversion and the hydrolysis catalyzed by certain proteolytic enzymes is referred to. Under the conditions of freeze drying are formed in hydrochloric acid solutions of DL-alanyl-DL-serine O-peptide and depsipeptide.

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Author:Hermann HartmannGND, Joachim HeidbergGND
Parent Title (German):Zeitschrift für Naturforschung, B
Publisher:Verlag der Zeitschrift für Naturforschung
Place of publication:Tübingen
Document Type:Article
Date of Publication (online):2014/06/02
Year of first Publication:1964
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2023/07/13
Page Number:6
First Page:1095
Last Page:1100
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung-Nicht kommerziell-Keine Bearbeitung 3.0