KINETICS AND MECHANISM OF THE CLEAVAGE OF THE PEPTIDE-BOND NEXT TO ASPARAGINE

Citation
S. Capasso et al., KINETICS AND MECHANISM OF THE CLEAVAGE OF THE PEPTIDE-BOND NEXT TO ASPARAGINE, Peptides, 17(6), 1996, pp. 1075-1077
Citations number
16
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Biology
Journal title
Peptides → ACNP
ISSN journal
0196-9781
Volume
17
Issue
6
Year of publication
1996
Pages
1075 - 1077
Database
ISI
SICI code
0196-9781(1996)17:6<1075:KAMOTC>2.0.ZU;2-Z
Abstract
The spontaneous cleavage reaction of the tetrapeptide Piv-Gly Asn-Sar- Gly-NHtBu to the C-terminal dipeptide and N-terminal succinimide dipep tide proceeds through pre-equilibrium deprotonation of the amide group of the asparagine side chain, Followed by intramolecular nucleophilic attack of nitrogen on the peptide carbonyl carbon atom. General acid- catalyzed breakdown of the intermediate then gives the products. Accor ding to this mechanism, the reaction rate strongly increases with pH a nd buffer concentration.