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Conformational preferences of proline analogues with a fused benzene ring
dc.contributor.author | Warren, Javier G. |
dc.contributor.author | Revilla López, Guillermo |
dc.contributor.author | Alemán Llansó, Carlos |
dc.contributor.author | Jimenez Sanz, Ana Isabel |
dc.contributor.author | Cativiela, Carlos |
dc.contributor.author | Torras Costa, Juan |
dc.contributor.other | Universitat Politècnica de Catalunya. Departament d'Enginyeria Química |
dc.date.accessioned | 2010-09-17T09:41:44Z |
dc.date.available | 2010-09-17T09:41:44Z |
dc.date.created | 2010-09-16 |
dc.date.issued | 2010-09-16 |
dc.identifier.citation | Warren, J.G. [et al.]. Conformational preferences of proline analogues with a fused benzene ring. "Journal of physical chemistry B", 16 Setembre 2010, vol. 114, núm. 36, p. 11761-11770. |
dc.identifier.issn | 1520-6106 |
dc.identifier.uri | http://hdl.handle.net/2117/8945 |
dc.description.abstract | The intrinsic conformational preferences of indoline-2-carboxylic acid (Inc) and its R-methylated derivative (RMeInc) have been investigated using quantum mechanical calculations. Specifically, the behavior of their N-acetyl-N′-methylamide derivatives, Ac-L-Inc-NHMe and Ac-L-RMeInc-NHMe, has been explored at the B3LYP/6-31+G(d,p) level. Such amino acids are analogues of proline and (R-methyl)proline, respectively, bearing a benzene ring fused to the Cγ-Cδ bond of the five-membered pyrrolidine ring. The additional aromatic group has been shown to significantly restrict the conformational space available to these residues by reducing the flexibility of both the five-membered cycle and the peptide backbone. The fused benzene ring also plays a critical role in determining the cis-trans arrangement of the amide bond involving the pyrrolidine nitrogen, which is also modulated by the presence of the R-methyl group in the RMeInc derivative. Furthermore, the influence of the environment on the conformational propensities of these compounds has been evaluated by using both a self-consistent reaction field model and a recently developed interface in a hybrid QM/MM scheme, in which the solvent molecules are treated explicitly with classical mechanics while the solute is described by quantum mechanics at the density functional theory level. |
dc.format.extent | 10 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 |
dc.title | Conformational preferences of proline analogues with a fused benzene ring |
dc.type | Article |
dc.subject.lemac | Aminoàcids |
dc.contributor.group | Universitat Politècnica de Catalunya. IMEM - Innovació, Modelització i Enginyeria en (BIO) Materials |
dc.identifier.doi | 10.1021/jp105456r |
dc.relation.publisherversion | http://pubs.acs.org/doi/abs/10.1021/jp105456r |
dc.rights.access | Restricted access - publisher's policy |
local.identifier.drac | 2743701 |
dc.description.version | Postprint (published version) |
local.citation.author | Warren, J.G.; Revilla-López, G.; Alemán, C.; Jimenez, Ana I; Cativiela, C.; Torras, J. |
local.citation.publicationName | Journal of physical chemistry B |
local.citation.volume | 114 |
local.citation.number | 36 |
local.citation.startingPage | 11761 |
local.citation.endingPage | 11770 |
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