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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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
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repository_id_str
spelling One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide CyclopeptidesSpengler, JanBlanco Canosa, Juan B.Forni, LucianoAlbericio, FernandoLigation–OxidativCyclopeptidesDisulfideNative 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.American Chemical Society2019-06-11T12:51:48Z2019-06-11T12:51:48Z2018info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfSpengler, J., Blanco Canosa, J. B., Forni, L., & Albericio, F. (2018). One-Pot Peptide Ligation–Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides. Organic letters, 20(14), 4306-4309. doi:10.1021/acs.orglett.8b01741.https://doi.org/10.1021/acs.orglett.8b01741http://repositorio.ikiam.edu.ec/jspui/handle/RD_IKIAM/213https://doi.org/10.1021/acs.orglett.8b01741enPRODUCCIÓN CIENTÍFICA-ARTÍCULOS;A-IKIAM-000150Atribución-NoComercial-SinDerivadas 3.0 Estados Unidos de Américahttp://creativecommons.org/licenses/by-nc-nd/3.0/us/info:eu-repo/semantics/openAccessreponame:Repositorio Universidad Regional Amazónicainstname:Universidad Regional Amazónicainstacron:IKIAM2022-06-04T08:03:15Zoai:repositorio.ikiam.edu.ec:RD_IKIAM/213Institucionalhttps://repositorio.ikiam.edu.ec/Universidad públicahttps://www.ikiam.edu.ec/https://repositorio.ikiam.edu.ec/oaiEcuador...opendoar:02022-06-04T08:03:15falseInstitucionalhttps://repositorio.ikiam.edu.ec/Universidad públicahttps://www.ikiam.edu.ec/https://repositorio.ikiam.edu.ec/oai.Ecuador...opendoar:02022-06-04T08:03:15Repositorio Universidad Regional Amazónica - Universidad Regional Amazónicafalse
dc.title.none.fl_str_mv One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
title One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
spellingShingle One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
Spengler, Jan
Ligation–Oxidativ
Cyclopeptides
Disulfide
title_short One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
title_full One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
title_fullStr One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
title_full_unstemmed One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
title_sort One-Pot Peptide Ligation – Oxidative Cyclization Protocol for the Preparation of Short/Medium Size Disulfide Cyclopeptides
dc.creator.none.fl_str_mv Spengler, Jan
Blanco Canosa, Juan B.
Forni, Luciano
Albericio, Fernando
author Spengler, Jan
author_facet Spengler, Jan
Blanco Canosa, Juan B.
Forni, Luciano
Albericio, Fernando
author_role author
author2 Blanco Canosa, Juan B.
Forni, Luciano
Albericio, Fernando
author2_role author
author
author
dc.subject.none.fl_str_mv Ligation–Oxidativ
Cyclopeptides
Disulfide
topic Ligation–Oxidativ
Cyclopeptides
Disulfide
description 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.
publishDate 2018
dc.date.none.fl_str_mv 2018
2019-06-11T12:51:48Z
2019-06-11T12:51:48Z
dc.type.none.fl_str_mv info:eu-repo/semantics/publishedVersion
info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv Spengler, J., Blanco Canosa, J. B., Forni, L., & Albericio, F. (2018). One-Pot Peptide Ligation–Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides. Organic letters, 20(14), 4306-4309. doi:10.1021/acs.orglett.8b01741.
https://doi.org/10.1021/acs.orglett.8b01741
http://repositorio.ikiam.edu.ec/jspui/handle/RD_IKIAM/213
https://doi.org/10.1021/acs.orglett.8b01741
identifier_str_mv Spengler, J., Blanco Canosa, J. B., Forni, L., & Albericio, F. (2018). One-Pot Peptide Ligation–Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides. Organic letters, 20(14), 4306-4309. doi:10.1021/acs.orglett.8b01741.
url https://doi.org/10.1021/acs.orglett.8b01741
http://repositorio.ikiam.edu.ec/jspui/handle/RD_IKIAM/213
dc.language.none.fl_str_mv en
language_invalid_str_mv en
dc.relation.none.fl_str_mv PRODUCCIÓN CIENTÍFICA-ARTÍCULOS;A-IKIAM-000150
dc.rights.none.fl_str_mv Atribución-NoComercial-SinDerivadas 3.0 Estados Unidos de América
http://creativecommons.org/licenses/by-nc-nd/3.0/us/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Atribución-NoComercial-SinDerivadas 3.0 Estados Unidos de América
http://creativecommons.org/licenses/by-nc-nd/3.0/us/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:Repositorio Universidad Regional Amazónica
instname:Universidad Regional Amazónica
instacron:IKIAM
instname_str Universidad Regional Amazónica
instacron_str IKIAM
institution IKIAM
reponame_str Repositorio Universidad Regional Amazónica
collection Repositorio Universidad Regional Amazónica
repository.name.fl_str_mv Repositorio Universidad Regional Amazónica - Universidad Regional Amazónica
repository.mail.fl_str_mv .
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score 15.301603

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