Site-selective modification of peptide backbones

The site-selective modification of peptide backbones allows an outstanding fine-tuning of peptide conformation, folding ability, and physico-chemical and biological properties. However, to achieve selectivity in the core of these biopolymers is challenging. In the last few years, many advances towar...

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Detalles Bibliográficos
Autores: Boto, Alicia, González Martín, Concepción C., Hernández, Dácil, Romero-Estudillo, Iván, Saavedra, Carlos J.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/252097
Acceso en línea:http://hdl.handle.net/10261/252097
Access Level:acceso abierto
Palabra clave:Site-selective
Peptide
Backbones
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spelling Site-selective modification of peptide backbonesBoto, AliciaGonzález Martín, Concepción C.Hernández, DácilRomero-Estudillo, IvánSaavedra, Carlos J.Site-selectivePeptideBackbonesThe site-selective modification of peptide backbones allows an outstanding fine-tuning of peptide conformation, folding ability, and physico-chemical and biological properties. However, to achieve selectivity in the core of these biopolymers is challenging. In the last few years, many advances towards this goal have been developed. This review addresses the selective modification of Cα- and N-positions, from the use of “customizable units” to the residue-directed introduction of substituents. The site-selective modification of the peptide bond, i.e. the formation of thioamides or heterocycles, which alters backbone rigidity and ability to form hydrogen bonds or recognition by enzymes, is also described. Moreover, not only the modifications in internal backbone positions, but also in the N- and C-termini are discussed. In addition to chemical methodologies, the review addresses some reactions, catalyzed by natural or engineered enzymes, that afford unprecedent regio- and stereoselectivity in backbone modifications.This work was mainly financed by project ProID2020010134 (Subvenciones a la Realización I + D Mª Carmen Betancourt y Molina, ACIISI-Gobierno de Canarias, with European Funds for Regional Development-FEDER) with contributions from project APOGEO (MAC/1.1.b./226, Cooperation Program INTERREG-MAC 2014–20 with FEDER funds, as well as Consejo Nacional de Ciencia y Tecnología (CONACYT, Mexico) through project 2015-01-807. D. H. also acknowledges her current contract (TRANSALUDAGRO) financed by Cabildo de Tenerife, Program TF INNOVA 2016-21 (with MEDI & FDCAN Funds). C. J. S. is currently recipient of a “Agustín de Betancourt”-Tenerife 2030 postdoctoral grant (Universidad de La Laguna-Cabildo de Tenerife, cofinanced by MEDI & FDCAN Funds). I. R-E. thanks CONACYT for Catedra contract 942.Peer reviewedRoyal Society of Chemistry (UK)Gobierno de CanariasAgencia Canaria de Investigación, Innovación y Sociedad de la InformaciónInterregConsejo Nacional de Ciencia y Tecnología (México)Cabildo de TenerifeUniversidad de La LagunaCSIC - Unidad de Recursos de Información Científica para la Investigación (URICI)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202120212021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_dcae04bcPublisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/252097reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.1039/D1QO00892GSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2520972026-05-22T06:33:51Z
dc.title.none.fl_str_mv Site-selective modification of peptide backbones
title Site-selective modification of peptide backbones
spellingShingle Site-selective modification of peptide backbones
Boto, Alicia
Site-selective
Peptide
Backbones
title_short Site-selective modification of peptide backbones
title_full Site-selective modification of peptide backbones
title_fullStr Site-selective modification of peptide backbones
title_full_unstemmed Site-selective modification of peptide backbones
title_sort Site-selective modification of peptide backbones
dc.creator.none.fl_str_mv Boto, Alicia
González Martín, Concepción C.
Hernández, Dácil
Romero-Estudillo, Iván
Saavedra, Carlos J.
author Boto, Alicia
author_facet Boto, Alicia
González Martín, Concepción C.
Hernández, Dácil
Romero-Estudillo, Iván
Saavedra, Carlos J.
author_role author
author2 González Martín, Concepción C.
Hernández, Dácil
Romero-Estudillo, Iván
Saavedra, Carlos J.
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Gobierno de Canarias
Agencia Canaria de Investigación, Innovación y Sociedad de la Información
Interreg
Consejo Nacional de Ciencia y Tecnología (México)
Cabildo de Tenerife
Universidad de La Laguna
CSIC - Unidad de Recursos de Información Científica para la Investigación (URICI)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Site-selective
Peptide
Backbones
topic Site-selective
Peptide
Backbones
description The site-selective modification of peptide backbones allows an outstanding fine-tuning of peptide conformation, folding ability, and physico-chemical and biological properties. However, to achieve selectivity in the core of these biopolymers is challenging. In the last few years, many advances towards this goal have been developed. This review addresses the selective modification of Cα- and N-positions, from the use of “customizable units” to the residue-directed introduction of substituents. The site-selective modification of the peptide bond, i.e. the formation of thioamides or heterocycles, which alters backbone rigidity and ability to form hydrogen bonds or recognition by enzymes, is also described. Moreover, not only the modifications in internal backbone positions, but also in the N- and C-termini are discussed. In addition to chemical methodologies, the review addresses some reactions, catalyzed by natural or engineered enzymes, that afford unprecedent regio- and stereoselectivity in backbone modifications.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_dcae04bc
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/252097
url http://hdl.handle.net/10261/252097
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://doi.org/10.1039/D1QO00892G
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Royal Society of Chemistry (UK)
publisher.none.fl_str_mv Royal Society of Chemistry (UK)
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812455

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