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DC Field | Value | Language |
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dc.contributor.author | Ramos Tomillero, Iván | - |
dc.contributor.author | Mendive Tapia, Lorena | - |
dc.contributor.author | Góngora Benítez, Miriam | - |
dc.contributor.author | Nicolás Galindo, Ernesto | - |
dc.contributor.author | Tulla-Puche, Judit | - |
dc.contributor.author | Albericio Palomera, Fernando | - |
dc.date.accessioned | 2020-03-11T16:19:36Z | - |
dc.date.available | 2020-03-11T16:19:36Z | - |
dc.date.issued | 2013-05-06 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/2445/152584 | - |
dc.description.abstract | Cys-disulfide bonds contribute to the stabilization of peptide and protein structures. The synthesis of these molecules requires a proper protection of Cys residues, which is crucial to prevent side-reactions and also to achieve the correct Cys connectivity. Here we undertook a mechanistic study of a set of well-known acid-labile Cys protecting groups, as well other new promising groups, in order to better understand the nature of their acid-lability. The stability of the carbocation generated during the acid treatment was found to have a direct impact on the removal of the protective groups from the corresponding protected Cys-containing peptides. Hence a combination of steric and conjugative effects determines the stability of the carbocations generated. Here we propose diphenylmethyl (Dpm) as a promising protecting group on the basis of its intermediate relative carbocation stability. All the optimized geometries and energies presented in this study were determined using a B3LYP/6-31G(d,p) calculation. The results discussed herein may be of broader applicability for the development of new protecting groups. | - |
dc.format.extent | 8 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | MDPI | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.3390/molecules18055155 | - |
dc.relation.ispartof | Molecules, 2013, vol. 18, num. 5, p. 5155-5162 | - |
dc.relation.uri | https://doi.org/10.3390/molecules18055155 | - |
dc.rights | cc-by (c) Ramos Tomillero, Iván et al., 2013 | - |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Síntesi de pèptids | - |
dc.subject.classification | Proteïnes | - |
dc.subject.classification | Cisteïna | - |
dc.subject.classification | Catàlisi | - |
dc.subject.other | Peptide synthesis | - |
dc.subject.other | Proteins | - |
dc.subject.other | Cysteine | - |
dc.subject.other | Catalysis | - |
dc.title | Understanding acid lability on Cysteine protecting groups | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 623954 | - |
dc.date.updated | 2020-03-11T16:19:36Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 23648593 | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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623954.pdf | 676.5 kB | Adobe PDF | View/Open |
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