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dc.contributor.authorMarafon, Giulia
dc.contributor.authorMoretto, Alessandro
dc.contributor.authorZanuy Gomara, David
dc.contributor.authorAlemán Llansó, Carlos
dc.contributor.authorCrisma, Marco
dc.contributor.authorToniolo, Claudio
dc.contributor.otherUniversitat Politècnica de Catalunya. Departament d'Enginyeria Química
dc.date.accessioned2020-05-05T12:04:57Z
dc.date.issued2019-11-26
dc.identifier.citationMarafon, G. [et al.]. Effect on the conformation of a terminally blocked, (E) ß,y-unsaturated o-amino acid residue induced by carbon methylation. "Journal of organic chemistry", 26 Novembre 2019, vol. 85, núm. 3, p. 1513-1524.
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/2117/186365
dc.description.abstractPeptides are well-known to play a fundamental therapeutic role and to represent building blocks for numerous useful biomaterials. Stabilizing their active 3D-structure by appropriate modifications remains, however, a challenge. In this study, we have expanded the available literature information on the conformational propensities of a promising backbone change of a terminally blocked d-amino acid residue, a dipeptide mimic, by replacing its central amide moiety with an (E) Cß-C¿ alkene unit. Specifically, we have examined by DFT calculations, X-ray diffraction in the crystalline state, and FT-IR absorption/NMR spectroscopies in solution the extended vs folded preferences of analogues of this prototype system either unmodified or possessing single or multiple methyl group substituents on each of its four -CH2-CH-CH-CH2– main-chain carbon atoms. The theoretical and experimental results obtained clearly point to the conclusion that increasing the number of adequately positioned methylations will enhance the preference of the original sequence to fold, thus opening interesting perspectives in the design of conformationally constrained peptidomimetics.
dc.format.extent12 p.
dc.language.isoeng
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Spain
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
dc.subjectÀrees temàtiques de la UPC::Enginyeria química::Química orgànica
dc.subject.lcshChemistry, Organic
dc.titleEffect on the conformation of a terminally blocked, (E) ß,y-unsaturated o-amino acid residue induced by carbon methylation
dc.typeArticle
dc.subject.lemacQuímica orgànica
dc.contributor.groupUniversitat Politècnica de Catalunya. IMEM-BRT- Innovation in Materials and Molecular Engineering - Biomaterials for Regenerative Therapies
dc.identifier.doi10.1021/acs.joc.9b02544
dc.relation.publisherversionhttps://pubs.acs.org/doi/abs/10.1021/acs.joc.9b02544
dc.rights.accessRestricted access - publisher's policy
local.identifier.drac26526993
dc.description.versionPostprint (author's final draft)
dc.date.lift2020-11-26
local.citation.authorMarafon, G.; Moretto, A.; Zanuy, D.; Aleman, C.; Crisma, M.; Toniolo, C.
local.citation.publicationNameJournal of organic chemistry
local.citation.volume85
local.citation.number3
local.citation.startingPage1513
local.citation.endingPage1524


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Except where otherwise noted, content on this work is licensed under a Creative Commons license : Attribution-NonCommercial-NoDerivs 3.0 Spain