One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides

Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitat...

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Detalles Bibliográficos
Autores: Spengler, Jan, Blanco Canosa, Juan B., Forni, Luciano, Albericio, Fernando
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:Ecuador
Institución:Universidad Regional Amazónica
Repositorio:Repositorio Universidad Regional Amazónica
OAI Identifier:oai:repositorio.ikiam.edu.ec:RD_IKIAM/213
Acceso en línea:https://doi.org/10.1021/acs.orglett.8b01741
http://repositorio.ikiam.edu.ec/jspui/handle/RD_IKIAM/213
Access Level:acceso abierto
Palabra clave:Ligation–Oxidativ
Cyclopeptides
Disulfide
Descripción
Sumario:Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercapto- phenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.