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Título

Effect of a β-phenyl substituent on the puckering modes of proline

Autor Calaza, M. Isabel ; Fatás, Paola ; Jiménez, Ana I. ; Cativiela, Carlos
Fecha de publicación 2013
Citación SMASH 2013
ResumenThe high significance of proline in peptide conformation and biology stimulates the development of proline analogues with tailored properties. The attachment of substituents to the five-membered ring is particularly atractive in this regard. Such substituents may serve to incorporate additional functionality as well as to modulate the conformational properties of proline. In this context, we have explored the effect produced by a phenyl substituent attached to the β-carbon atom of proline on the puckering modes adopted by the pyrrolidine ring. Both the cis and trans configurations of the β-phenyl group relative to the carbonyl moiety have been considered. The puckering modes of such proline analogues, cis- and trans-β-phenylproline, have been examined by NMR when incorporated into model dipeptides. We observed that the pyrrolidine conformation is significantly affected by the presence of the β-phenyl group. Those conformations that alleviate most the steric hindrance introduced by the bulky phenyl substituent are preferred. The orientation adopted by the aromatic moiety is much more restricted in the cis isomer. Thus, cis-β-phenylproline shows a highly marked propensity to adopt a Cγ-endo arrangement. In contrast, the trans derivative exhibits a higher flexibility, with Cγ-endo and Cγ-exo pyrrolidine shapes being accessible, as for proline itself.
Descripción Trabajo presentado a la Small Molecule NMR Conference celebrada en Santiago de Compostela (España) del 22 al 25 de septiembre de 2013.
URI http://hdl.handle.net/10261/112234
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