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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/1813
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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 Técnicas2025-09-29T10:12:45Zoai: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:34982025-09-29 10:12:45.289CONICET 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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1844614036577058816 |
score |
13.070432 |