Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library

Autores
Giudicessi, Silvana Laura; Gurevich Messina, Juan Manuel; Martínez Ceron, María Camila; Erra Balsells, Rosa; Albericio, F.; Cascone, Osvaldo; Camperi, Silvia Andrea
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
One bead−one peptide libraries allow the screening of suitable ligands for any target protein. Short cyclic peptides are ideal ligands for affinity chromatography because of their high affinity and selectivity for the target protein and stability against proteases. We designed a library synthesis strategy to facilitate the identification of cyclic peptides by MS consisting of (a) sequential incorporation of a mixture of Fmoc-Ala-OH and Fmoc-Asp[2-phenylisopropyl (OPp)]-OH (15:85) to Gly-oxymethylbenzamide-ChemMatrix (Gly-HMBA-CM) resin, (b) synthesis of the combinatorial library on the resin by the divide−couple−recombine method, (c) removal of OPp with 4% TFA, (d) peptide cyclization on solid phase through side-chain Asp and amino terminus, and (e) removal of side chain protecting groups with a 95% TFA cocktail. Peptides were cleaved from the beads with ammonia and the linear code was sequenced by MALDI-TOF MS/MS. The high capacity of ChemMatrix resin together with the sensitivity of MS allows code sequencing from a single bead.
Fil: Giudicessi, Silvana Laura. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Gurevich Messina, Juan Manuel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina;
Fil: Martínez Ceron, María Camila. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Albericio, F.. Instituto de Investigación Biomédica; España; Universidad de Barcelona; España; Centro de Investigación Biomédica en Red en Bioingeniería, Biomateriales y Nanomedicina; España;
Fil: Cascone, Osvaldo. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Camperi, Silvia Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Materia
Combinatorial Chemistry
Maldi-Tof Ms/Ms
Peptide Sequencing
2-Phenylisopropyl
Affinity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/1813
Acceder
id CONICETDig_bc0221405b1841a5aad95a3a40ff9345
oai_identifier_str oai:ri.conicet.gov.ar:11336/1813
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide LibraryGiudicessi, Silvana LauraGurevich Messina, Juan ManuelMartínez Ceron, María CamilaErra Balsells, RosaAlbericio, F.Cascone, OsvaldoCamperi, Silvia AndreaCombinatorial ChemistryMaldi-Tof Ms/MsPeptide Sequencing2-PhenylisopropylAffinityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1One bead−one peptide libraries allow the screening of suitable ligands for any target protein. Short cyclic peptides are ideal ligands for affinity chromatography because of their high affinity and selectivity for the target protein and stability against proteases. We designed a library synthesis strategy to facilitate the identification of cyclic peptides by MS consisting of (a) sequential incorporation of a mixture of Fmoc-Ala-OH and Fmoc-Asp[2-phenylisopropyl (OPp)]-OH (15:85) to Gly-oxymethylbenzamide-ChemMatrix (Gly-HMBA-CM) resin, (b) synthesis of the combinatorial library on the resin by the divide−couple−recombine method, (c) removal of OPp with 4% TFA, (d) peptide cyclization on solid phase through side-chain Asp and amino terminus, and (e) removal of side chain protecting groups with a 95% TFA cocktail. Peptides were cleaved from the beads with ammonia and the linear code was sequenced by MALDI-TOF MS/MS. The high capacity of ChemMatrix resin together with the sensitivity of MS allows code sequencing from a single bead.Fil: Giudicessi, Silvana Laura. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;Fil: Gurevich Messina, Juan Manuel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina;Fil: Martínez Ceron, María Camila. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;Fil: Albericio, F.. Instituto de Investigación Biomédica; España; Universidad de Barcelona; España; Centro de Investigación Biomédica en Red en Bioingeniería, Biomateriales y Nanomedicina; España;Fil: Cascone, Osvaldo. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;Fil: Camperi, Silvia Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;ACS Publications2013-09-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/1813Giudicessi, Silvana Laura; Gurevich Messina, Juan Manuel; Martínez Ceron, María Camila; Erra Balsells, Rosa; Albericio, F.; et al.; Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library; ACS Publications; ACS Combinatorial Science; 15; 10; 6-9-2013; 525-5292156-89522156-8944enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co400039ainfo:eu-repo/semantics/altIdentifier/doi/DOI:10.1021/co400039ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:42:35Zoai:ri.conicet.gov.ar:11336/1813instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:42:36.189CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
title Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
spellingShingle Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
Giudicessi, Silvana Laura
Combinatorial Chemistry
Maldi-Tof Ms/Ms
Peptide Sequencing
2-Phenylisopropyl
Affinity
title_short Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
title_full Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
title_fullStr Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
title_full_unstemmed Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
title_sort Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library
dc.creator.none.fl_str_mv Giudicessi, Silvana Laura
Gurevich Messina, Juan Manuel
Martínez Ceron, María Camila
Erra Balsells, Rosa
Albericio, F.
Cascone, Osvaldo
Camperi, Silvia Andrea
author Giudicessi, Silvana Laura
author_facet Giudicessi, Silvana Laura
Gurevich Messina, Juan Manuel
Martínez Ceron, María Camila
Erra Balsells, Rosa
Albericio, F.
Cascone, Osvaldo
Camperi, Silvia Andrea
author_role author
author2 Gurevich Messina, Juan Manuel
Martínez Ceron, María Camila
Erra Balsells, Rosa
Albericio, F.
Cascone, Osvaldo
Camperi, Silvia Andrea
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Combinatorial Chemistry
Maldi-Tof Ms/Ms
Peptide Sequencing
2-Phenylisopropyl
Affinity
topic Combinatorial Chemistry
Maldi-Tof Ms/Ms
Peptide Sequencing
2-Phenylisopropyl
Affinity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv One bead−one peptide libraries allow the screening of suitable ligands for any target protein. Short cyclic peptides are ideal ligands for affinity chromatography because of their high affinity and selectivity for the target protein and stability against proteases. We designed a library synthesis strategy to facilitate the identification of cyclic peptides by MS consisting of (a) sequential incorporation of a mixture of Fmoc-Ala-OH and Fmoc-Asp[2-phenylisopropyl (OPp)]-OH (15:85) to Gly-oxymethylbenzamide-ChemMatrix (Gly-HMBA-CM) resin, (b) synthesis of the combinatorial library on the resin by the divide−couple−recombine method, (c) removal of OPp with 4% TFA, (d) peptide cyclization on solid phase through side-chain Asp and amino terminus, and (e) removal of side chain protecting groups with a 95% TFA cocktail. Peptides were cleaved from the beads with ammonia and the linear code was sequenced by MALDI-TOF MS/MS. The high capacity of ChemMatrix resin together with the sensitivity of MS allows code sequencing from a single bead.
Fil: Giudicessi, Silvana Laura. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Gurevich Messina, Juan Manuel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina;
Fil: Martínez Ceron, María Camila. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Albericio, F.. Instituto de Investigación Biomédica; España; Universidad de Barcelona; España; Centro de Investigación Biomédica en Red en Bioingeniería, Biomateriales y Nanomedicina; España;
Fil: Cascone, Osvaldo. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
Fil: Camperi, Silvia Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Microbiología, Inmunología y Biotecnología; Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina;
description One bead−one peptide libraries allow the screening of suitable ligands for any target protein. Short cyclic peptides are ideal ligands for affinity chromatography because of their high affinity and selectivity for the target protein and stability against proteases. We designed a library synthesis strategy to facilitate the identification of cyclic peptides by MS consisting of (a) sequential incorporation of a mixture of Fmoc-Ala-OH and Fmoc-Asp[2-phenylisopropyl (OPp)]-OH (15:85) to Gly-oxymethylbenzamide-ChemMatrix (Gly-HMBA-CM) resin, (b) synthesis of the combinatorial library on the resin by the divide−couple−recombine method, (c) removal of OPp with 4% TFA, (d) peptide cyclization on solid phase through side-chain Asp and amino terminus, and (e) removal of side chain protecting groups with a 95% TFA cocktail. Peptides were cleaved from the beads with ammonia and the linear code was sequenced by MALDI-TOF MS/MS. The high capacity of ChemMatrix resin together with the sensitivity of MS allows code sequencing from a single bead.
publishDate 2013
dc.date.none.fl_str_mv 2013-09-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/1813
Giudicessi, Silvana Laura; Gurevich Messina, Juan Manuel; Martínez Ceron, María Camila; Erra Balsells, Rosa; Albericio, F.; et al.; Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library; ACS Publications; ACS Combinatorial Science; 15; 10; 6-9-2013; 525-529
2156-8952
2156-8944
url http://hdl.handle.net/11336/1813
identifier_str_mv Giudicessi, Silvana Laura; Gurevich Messina, Juan Manuel; Martínez Ceron, María Camila; Erra Balsells, Rosa; Albericio, F.; et al.; Friendly Strategy to Prepare Encoded One Bead−One Compound Cyclic Peptide Library; ACS Publications; ACS Combinatorial Science; 15; 10; 6-9-2013; 525-529
2156-8952
2156-8944
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co400039a
info:eu-repo/semantics/altIdentifier/doi/DOI:10.1021/co400039a
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv ACS Publications
publisher.none.fl_str_mv ACS Publications
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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