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http://hdl.handle.net/2445/99326
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DC Field | Value | Language |
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dc.contributor.author | López Martínez, Carlos | - |
dc.contributor.author | Flores-Morales, P. | - |
dc.contributor.author | Cruz, M. | - |
dc.contributor.author | Gonzalez, Teresa | - |
dc.contributor.author | Feliz Rodenas, Miguel | - |
dc.contributor.author | Diez Pascual, Anna | - |
dc.contributor.author | Campanera Alsina, Josep Maria | - |
dc.date.accessioned | 2016-06-07T16:33:12Z | - |
dc.date.available | 2017-03-18T23:01:28Z | - |
dc.date.issued | 2016-03-18 | - |
dc.identifier.issn | 1463-9076 | - |
dc.identifier.uri | http://hdl.handle.net/2445/99326 | - |
dc.description.abstract | Cis and trans proline conformers are often associated with dramatic changes in the biological function of peptides. A slow equilibrium between cis and trans Ile-Pro amide bond conformers occurs in constrained derivatives of the native marine cyclic heptapeptide stylostatin 1 (cyclo-(NSLAIPF)), a potential anticancer agent. In this work, four cyclopeptides, cyclo-(NSTAIPF), cyclo-(KSTAIPF), cyclo-(RSTAIPF) and cyclo-(DSTAIPF), which are structurally related to stylostatin 1, are experimentally and computationally examined in order to assess the effect of residue mutations on the cis-trans conformational ratio and the apparent capacity to form dimeric aggregates. Primarily, cyclo-(KSTAIPF) and cyclo-(RSTAIPF) showed specific trends in circular dichroism, MALDI-TOF and HPLC purification experiments, which suggests the occurrence of peptide dimerization. Meanwhile, the NMR spectrum of cyclo-(KSTAIPF) indicates that this cyclopeptide exists in the two slow-exchange families of conformations mentioned above. Molecular dynamics simulations combined with quantum mechanical calculations have shed light on the factors governing the cis/trans conformational ratio. In particular, we have found that residue mutations affect the internal hydrogen bond pattern which ultimately tunes the cis/trans conformational ratio and that only trans conformers are capable of aggregating due to the shape complementarity of the two subunits. | - |
dc.format.extent | 13 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry | - |
dc.relation.isformatof | Versió postprint del document publicat a: http://dx.doi.org/10.1039/c5cp05937b | - |
dc.relation.ispartof | Physical Chemistry Chemical Physics, 2016, vol. 18, num. 18, p. 12755-12767 | - |
dc.relation.uri | http://dx.doi.org/10.1039/c5cp05937b | - |
dc.rights | (c) Lopez-Martinez, C. et al., 2016 | - |
dc.source | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) | - |
dc.subject.classification | Química orgànica | - |
dc.subject.classification | Pèptids | - |
dc.subject.other | Organic chemistry | - |
dc.subject.other | Peptides | - |
dc.title | Proline cis-trans isomerization and its implications for the dimerization of analogues of cyclopeptide stylostatin 1: a combined computational and experimental study | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 659424 | - |
dc.date.updated | 2016-06-07T16:33:17Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 27097793 | - |
Appears in Collections: | Articles publicats en revistes (Institut de Biomedicina (IBUB)) Articles publicats en revistes (Centres Científics i Tecnològics de la Universitat de Barcelona (CCiTUB)) Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) |
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File | Description | Size | Format | |
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659424.pdf | 2.52 MB | Adobe PDF | View/Open |
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