TY  - JOUR
A1  - Hartmann, Hermann
A1  - Heidberg, Joachim
T1  - Untersuchungen über die Kinetik der Spaltung von Di- und Tripeptiden
III. Mitt.: Über die rasche Spaltung von Serinpeptiden in rein wässriger Lösung
T2  - Zeitschrift für Naturforschung, B
N2  - 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.
Y1  - 2014
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/71336
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-713361
SN  - 1865-7117
SN  - 0932-0776
VL  - 19
IS  - 12
SP  - 1095
EP  - 1100
PB  - Verlag der Zeitschrift für Naturforschung
CY  - Tübingen
ER  -