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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/52533
Title: Conformational Preferences of Proline Analogues with a Fused Benzene Ring
Authors: Warren, Javier G.; Alemán, Carlos; Jiménez, Ana I.; Cativiela, Carlos
Issue Date: 2010
Publisher: American Chemical Society
Citation: Journal of Physical Chemistry B 114(36): 11761-11770 (2010)
Abstract: The intrinsic conformational preferences of indoline-2-carboxylic acid (Inc) and its α-methylated derivative (αMeInc) have been investigated using quantum mechanical calculations. Specifically, the behavior of their N-acetyl-N′-methylamide derivatives, Ac-l-Inc-NHMe and Ac-l-αMeInc-NHMe, has been explored at the B3LYP/6-31+G(d,p) level. Such amino acids are analogues of proline and (α-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 α-methyl group in the αMeInc 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.
URI: http://hdl.handle.net/10261/52533
DOI: 10.1021/jp105456r
Identifiers: doi: 10.1021/jp105456r
issn: 1520-6106
e-issn: 1520-5207
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