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Effect on the conformation of a terminally blocked, (E) ß,y-unsaturated o-amino acid residue induced by carbon methylation
dc.contributor.author | Marafon, Giulia |
dc.contributor.author | Moretto, Alessandro |
dc.contributor.author | Zanuy Gomara, David |
dc.contributor.author | Alemán Llansó, Carlos |
dc.contributor.author | Crisma, Marco |
dc.contributor.author | Toniolo, Claudio |
dc.contributor.other | Universitat Politècnica de Catalunya. Departament d'Enginyeria Química |
dc.date.accessioned | 2020-05-05T12:04:57Z |
dc.date.available | 2020-11-26T01:28:04Z |
dc.date.issued | 2019-11-26 |
dc.identifier.citation | Marafon, 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.issn | 0022-3263 |
dc.identifier.uri | http://hdl.handle.net/2117/186365 |
dc.description.abstract | Peptides 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.extent | 12 p. |
dc.language.iso | eng |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Spain |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/es/ |
dc.subject | Àrees temàtiques de la UPC::Enginyeria química::Química orgànica |
dc.subject.lcsh | Chemistry, Organic |
dc.title | Effect on the conformation of a terminally blocked, (E) ß,y-unsaturated o-amino acid residue induced by carbon methylation |
dc.type | Article |
dc.subject.lemac | Química orgànica |
dc.contributor.group | Universitat Politècnica de Catalunya. IMEM-BRT- Innovation in Materials and Molecular Engineering - Biomaterials for Regenerative Therapies |
dc.identifier.doi | 10.1021/acs.joc.9b02544 |
dc.relation.publisherversion | https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b02544 |
dc.rights.access | Open Access |
local.identifier.drac | 26526993 |
dc.description.version | Postprint (author's final draft) |
local.citation.author | Marafon, G.; Moretto, A.; Zanuy, D.; Aleman, C.; Crisma, M.; Toniolo, C. |
local.citation.publicationName | Journal of organic chemistry |
local.citation.volume | 85 |
local.citation.number | 3 |
local.citation.startingPage | 1513 |
local.citation.endingPage | 1524 |
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