Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides

While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated impro...

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Detalles Bibliográficos
Autores: García Pindado, Júlia, Willemse, Tom, Goss, Rebecca, Maes, Bert U. W., Giralt Lledó, Ernest, Ballet, Steven, Teixidó Turà, Meritxell
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/121062
Acceso en línea:https://hdl.handle.net/2445/121062
Access Level:acceso abierto
Palabra clave:Pèptids
Triptòfan
Peptides
Tryptophan
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spelling Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptidesGarcía Pindado, JúliaWillemse, TomGoss, RebeccaMaes, Bert U. W.Giralt Lledó, ErnestBallet, StevenTeixidó Turà, MeritxellPèptidsTriptòfanPeptidesTryptophanWhile revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on‐resin Suzuki‐Miyaura cross‐coupling reactions.John Wiley & Sons2018201920182018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion24 p.application/pdfhttps://hdl.handle.net/2445/121062Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: http://dx.doi.org/10.1002/bip.23112Biopolymers, 2018http://dx.doi.org/10.1002/bip.23112(c) Wiley, 2018info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1210622026-05-29T05:05:01Z
dc.title.none.fl_str_mv Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
spellingShingle Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
García Pindado, Júlia
Pèptids
Triptòfan
Peptides
Tryptophan
title_short Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_full Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_fullStr Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_full_unstemmed Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_sort Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
dc.creator.none.fl_str_mv García Pindado, Júlia
Willemse, Tom
Goss, Rebecca
Maes, Bert U. W.
Giralt Lledó, Ernest
Ballet, Steven
Teixidó Turà, Meritxell
author García Pindado, Júlia
author_facet García Pindado, Júlia
Willemse, Tom
Goss, Rebecca
Maes, Bert U. W.
Giralt Lledó, Ernest
Ballet, Steven
Teixidó Turà, Meritxell
author_role author
author2 Willemse, Tom
Goss, Rebecca
Maes, Bert U. W.
Giralt Lledó, Ernest
Ballet, Steven
Teixidó Turà, Meritxell
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Pèptids
Triptòfan
Peptides
Tryptophan
topic Pèptids
Triptòfan
Peptides
Tryptophan
description While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on‐resin Suzuki‐Miyaura cross‐coupling reactions.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018
2018
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/121062
url https://hdl.handle.net/2445/121062
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1002/bip.23112
Biopolymers, 2018
http://dx.doi.org/10.1002/bip.23112
dc.rights.none.fl_str_mv (c) Wiley, 2018
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley, 2018
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 24 p.
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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