Long-range intramolecular S â N acyl migration: a study of the formation of native peptide analogues via 13-, 15-, and 16-membered cyclic transition states.
J Org Chem
; 77(6): 2637-48, 2012 Mar 16.
Article
em En
| MEDLINE
| ID: mdl-22283871
ABSTRACT
The intramolecular long-range S â N acyl migration via 13-, 15-, and 16-membered cyclic transition states to form native tetra- and pentapeptide analogues was studied on S-acylcysteine peptides containing ß- or γ-amino acids. The pH-dependency study of the acyl migration via a 15-membered cyclic transition state indicated that the reaction is favored at a pH range from 7.0 to 7.6. Experimental observations are supported by structural and computational investigations.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Oligopeptídeos
/
Peptídeos
/
Cisteína
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article