Ítem
Solo Metadatos

p-Methoxyphenol: A potent and effective scavenger for solid-phase peptide synthesis

Mostrar el registro sencillo de la publicación
dc.creatorSamacá, Jhoanspa
dc.creatorVelandia?Bautista, Erikaspa
dc.creatorTabares, Luisaspa
dc.creatorEscamilla, Luisspa
dc.creatorVanegas, Magnoliaspa
dc.creatorPatarroyo, Manuel?E.spa
dc.date.accessioned2020-05-25T23:56:27Z
dc.date.available2020-05-25T23:56:27Z
dc.date.created2020spa
dc.description.abstractDuring the final step of t-Boc/Bzl, solid-phase peptide synthesis (SPPS)-protecting groups from amino acids (aa) side chains must be removed from the target peptides during cleavage from the solid support. These reaction steps involve hydrolysis with hydrogen fluoride (HF) in the presence of a nucleophile (scavenger), whose function is to trap the carbocations produced during SN1-type reactions. Five peptide sequences were synthesised for evaluating p-methoxyphenol effectiveness as a potent scavenger. After the synthesis, the resin–peptide was then separated into two equal parts to be cleaved using two scavengers: conventional reactive p-cresol (reported in the literature as an effective acyl ion eliminator) and p-methoxyphenol (hypothesised as fulfilling the same functions as the routinely used scavenger). Detailed analysis of the electrostatic potential map (EPM) revealed similarities between these two nucleophiles, regarding net atomic charge, electron density distribution, and similar pKa values. Good scavenger efficacy was observed by chromatography and mass spectrometry results for the synthesised molecules, which revealed that p-methoxyphenol can be used as a potent scavenger during SPPS by t-Boc/Bzl strategy, as similar results were obtained using the conventional scavenger. © 2020 European Peptide Society and John Wiley and Sons, Ltd.eng
dc.format.mimetypeapplication/pdf
dc.identifier.doihttps://doi.org/10.1002/psc.3251
dc.identifier.issn10752617
dc.identifier.issn10991387
dc.identifier.urihttps://repository.urosario.edu.co/handle/10336/22427
dc.language.isoengspa
dc.publisherJohn Wiley and Sons Ltdspa
dc.relation.citationTitleJournal of Peptide Science
dc.relation.ispartofJournal of Peptide Science, ISSN:10752617, 10991387,(2020)spa
dc.relation.urihttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85082922235&doi=10.1002%2fpsc.3251&partnerID=40&md5=857facf6166a5f33e52db80a48fdbe4fspa
dc.rights.accesRightsinfo:eu-repo/semantics/openAccess
dc.rights.accesoAbierto (Texto Completo)spa
dc.source.instnameinstname:Universidad del Rosariospa
dc.source.reponamereponame:Repositorio Institucional EdocURspa
dc.subject.keywordCleavagespa
dc.subject.keywordP-cresolspa
dc.subject.keywordP-methoxyphenolspa
dc.subject.keywordScavengerspa
dc.subject.keywordSolid-phase peptide synthesisspa
dc.subject.keywordT-boc/bzl strategyspa
dc.titlep-Methoxyphenol: A potent and effective scavenger for solid-phase peptide synthesisspa
dc.typearticleeng
dc.type.hasVersioninfo:eu-repo/semantics/publishedVersion
dc.type.spaArtículospa
Archivos
Colecciones
Artículos