Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine

A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino aci...

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Detalles Bibliográficos
Autores: Ng-Choi, Iteng, Oliveras Rovira, Àngel, Feliu Soley, Lidia, Planas i Grabuleda, Marta
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2019
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:10256/16557
Acceso en línea:http://hdl.handle.net/10256/16557
Access Level:acceso abierto
Palabra clave:Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
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spelling Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanineNg-Choi, ItengOliveras Rovira, ÀngelFeliu Soley, LidiaPlanas i Grabuleda, MartaAntibiòtics pèptidsPeptide antibioticsPèptids -- SíntesiPeptides -- SynthesisA methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki-Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptidesThis work was supported by the Ministerio de Economía y Competitividad (MINECO) [grant numbers AGL2009-13255-C02-02/AGR, AGL2012-39880-C02-02 and AGL2015-69876-C2-2-R]Beilstein-InstitutMinisterio de Ciencia e Innovación (Espanya)Ministerio de Economía y Competitividad (Espanya)2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewed8 p.application/pdfhttp://hdl.handle.net/10256/16557Beilstein Journal of Organic Chemistry, 2019, vol. 15, p. 761-768Articles publicats (D-Q)Ng-Choi, Iteng Oliveras Rovira, Àngel Feliu Soley, Lídia Planas i Grabuleda, Marta 2019 Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine Beilstein Journal of Organic Chemistry 15 761 768reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.15.72info:eu-repo/semantics/altIdentifier/eissn/1860-5397info:eu-repo/semantics/altIdentifier/eissn/1860-5397info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02info:eu-repo/grantAgreement/MINECO//AGL2015-69876-C2-2-RAttribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/165572026-05-29T05:05:01Z
dc.title.none.fl_str_mv Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
title Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
spellingShingle Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
Ng-Choi, Iteng
Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
title_short Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
title_full Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
title_fullStr Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
title_full_unstemmed Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
title_sort Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine
dc.creator.none.fl_str_mv Ng-Choi, Iteng
Oliveras Rovira, Àngel
Feliu Soley, Lidia
Planas i Grabuleda, Marta
author Ng-Choi, Iteng
author_facet Ng-Choi, Iteng
Oliveras Rovira, Àngel
Feliu Soley, Lidia
Planas i Grabuleda, Marta
author_role author
author2 Oliveras Rovira, Àngel
Feliu Soley, Lidia
Planas i Grabuleda, Marta
author2_role author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
Ministerio de Economía y Competitividad (Espanya)
dc.subject.none.fl_str_mv Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
topic Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
description A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki-Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides
publishDate 2019
dc.date.none.fl_str_mv 2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/16557
url http://hdl.handle.net/10256/16557
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.15.72
info:eu-repo/semantics/altIdentifier/eissn/1860-5397
info:eu-repo/semantics/altIdentifier/eissn/1860-5397
info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02
info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02
info:eu-repo/grantAgreement/MINECO//AGL2015-69876-C2-2-R
dc.rights.none.fl_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 8 p.
application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
dc.source.none.fl_str_mv Beilstein Journal of Organic Chemistry, 2019, vol. 15, p. 761-768
Articles publicats (D-Q)
Ng-Choi, Iteng Oliveras Rovira, Àngel Feliu Soley, Lídia Planas i Grabuleda, Marta 2019 Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine Beilstein Journal of Organic Chemistry 15 761 768
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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