Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group inN-Protected Peptides under Mild Basic Conditions
Ver/ Abrir
Impacto
Scholar |
Otros documentos de la autoría: Tena Solsona, Marta; Angulo-Pachón, César A.; Escuder, Beatriu; Miravet, Juan
Metadatos
Mostrar el registro completo del ítemcomunitat-uji-handle:10234/9
comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
comunitat-uji-handle4:
INVESTIGACIONMetadatos
Título
Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group inN-Protected Peptides under Mild Basic ConditionsFecha de publicación
2014Editor
Wiley Online LibraryISSN
1099-0690Tipo de documento
info:eu-repo/semantics/articlePalabras clave / Materias
Resumen
The unexpected lability of Z protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilizes the tetra ... [+]
The unexpected lability of Z protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilizes the tetrahedral intermediate formed after the nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N-protected tripeptides and tetrapeptides but Z-protected dipeptides are stable under the same conditions due to the blockage of the vicinal amide NH by intramolecular H-bonding with terminal carboxylate moiety. [-]
Publicado en
European Journal of Organic Chemistry, 2014(16)Derechos de acceso
This is the pre-peer reviewed version of the following article:TENA‐SOLSONA, Marta, et al. Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group in N‐Protected Peptides under Mild Basic Conditions. European Journal of Organic Chemistry, 2014, vol. 2014, no 16, p. 3372-3378, which has been published in final form at [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201400154/abstract]
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
Aparece en las colecciones
- QUIO_Articles [689]