Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins

An efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe−Tyr, a Tyr−Tyr, o...

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Autores: Ng-Choi, Iteng, Figueras, Eduard, Oliveras Rovira, Àngel, Feliu Soley, Lidia, Planas i Grabuleda, Marta
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2020
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/18665
Acesso em linha:http://hdl.handle.net/10256/18665
Access Level:Acceso aberto
Palavra-chave:Pèptids
Síntesi en fase sólida
Peptides
Solid-phase synthesis
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spelling Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycinsNg-Choi, ItengFigueras, EduardOliveras Rovira, ÀngelFeliu Soley, LidiaPlanas i Grabuleda, MartaPèptidsSíntesi en fase sólidaPeptidesSolid-phase synthesisAn efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe−Tyr, a Tyr−Tyr, or a His−Tyr linkage. This methodology first involved an intramolecular Suzuki−Miyaura arylation of a linear peptidyl resin incorporating the corresponding halogenated amino acid at the N-terminus and a boronotyrosine at the C-terminus. After N-methylation of the resulting biaryl cyclic peptidyl resin, the N-methylated lipopeptidyl tail was then assembled. The biaryl cyclic lipopeptides were purified and characterizedThis work was supported by Grants AGL2009-13255-C02-02/AGR, AGL2012-39880-C02-02/AGR, MPCUdG2016/038, and RTI2018-099410-B-C22 (MCIU/ AEI/FEDER, EU)American Chemical Society (ACS)Agencia Estatal de InvestigaciónMinisterio de Economía y Competitividad (Espanya)Ministerio de Ciencia e Innovación (Espanya)2020info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewed12 p.application/pdfhttp://hdl.handle.net/10256/18665© ACS Omega, 2020, vol. 5, núm. 36, p. 23401-23412Articles publicats (D-Q)Ng-Choi, Iteng Figueras, Eduard Oliveras Rovira, Àngel Feliu Soley, Lídia Planas i Grabuleda, Marta 2020 Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins ACS Omega 5 36 23401 23412reponame: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/10.1021/acsomega.0c03352info:eu-repo/semantics/altIdentifier/eissn/2470-1343info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-099410-B-C22ACS Choice Licenseinfo:eu-repo/semantics/openAccessoai:recercat.cat:10256/186652026-05-29T05:05:01Z
dc.title.none.fl_str_mv Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
title Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
spellingShingle Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
Ng-Choi, Iteng
Pèptids
Síntesi en fase sólida
Peptides
Solid-phase synthesis
title_short Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
title_full Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
title_fullStr Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
title_full_unstemmed Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
title_sort Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins
dc.creator.none.fl_str_mv Ng-Choi, Iteng
Figueras, Eduard
Oliveras Rovira, Àngel
Feliu Soley, Lidia
Planas i Grabuleda, Marta
author Ng-Choi, Iteng
author_facet Ng-Choi, Iteng
Figueras, Eduard
Oliveras Rovira, Àngel
Feliu Soley, Lidia
Planas i Grabuleda, Marta
author_role author
author2 Figueras, Eduard
Oliveras Rovira, Àngel
Feliu Soley, Lidia
Planas i Grabuleda, Marta
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Agencia Estatal de Investigación
Ministerio de Economía y Competitividad (Espanya)
Ministerio de Ciencia e Innovación (Espanya)
dc.subject.none.fl_str_mv Pèptids
Síntesi en fase sólida
Peptides
Solid-phase synthesis
topic Pèptids
Síntesi en fase sólida
Peptides
Solid-phase synthesis
description An efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe−Tyr, a Tyr−Tyr, or a His−Tyr linkage. This methodology first involved an intramolecular Suzuki−Miyaura arylation of a linear peptidyl resin incorporating the corresponding halogenated amino acid at the N-terminus and a boronotyrosine at the C-terminus. After N-methylation of the resulting biaryl cyclic peptidyl resin, the N-methylated lipopeptidyl tail was then assembled. The biaryl cyclic lipopeptides were purified and characterized
publishDate 2020
dc.date.none.fl_str_mv 2020
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/10256/18665
url http://hdl.handle.net/10256/18665
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.0c03352
info:eu-repo/semantics/altIdentifier/eissn/2470-1343
info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02
info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-099410-B-C22
dc.rights.none.fl_str_mv ACS Choice License
info:eu-repo/semantics/openAccess
rights_invalid_str_mv ACS Choice License
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 12 p.
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
dc.source.none.fl_str_mv © ACS Omega, 2020, vol. 5, núm. 36, p. 23401-23412
Articles publicats (D-Q)
Ng-Choi, Iteng Figueras, Eduard Oliveras Rovira, Àngel Feliu Soley, Lídia Planas i Grabuleda, Marta 2020 Solid-phase synthesis of biaryl cyclic lipopeptides derived from arylomycins ACS Omega 5 36 23401 23412
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 15,81155

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