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dc.contributor.authorAlemán Llansó, Carlos
dc.contributor.authorJimenez, Ana I
dc.contributor.authorCativiela, Carlos
dc.contributor.authorNussinov, Ruth
dc.contributor.authorCasanovas, Jordi
dc.contributor.otherUniversitat Politècnica de Catalunya. Departament d'Enginyeria Química
dc.identifier.citationAlemán, C. [et al.]. Conformational Preferences of 1-Amino-2-phenylcyclohexanecarboxylic Acid, a Phenylalanine Cyclohexane Analogue. "Journal of organic chemistry", Octubre 2009, vol. 74, núm. 20, p. 7834-7843.
dc.description.abstractThe intrinsic conformational preferences of the restricted phenylalanine analogue generated by including the R and β carbon atoms into a cyclohexane ring (1-amino-2-phenylcyclohexanecarboxylic acid, c6Phe) have been determined using quantum mechanical calculations. Specifically, the conformational profile of the N-acetyl-N0-methylamide derivative of the c6Phe stereoisomers exhibiting either a cis or a trans relative orientation between the amino and phenyl substituents has been analyzed in different environments (gas phase, chloroform, and aqueous solutions). Calculations were performed using B3LYP, MP2, and HF methods combined with the 6-31+ G(d,p) and 6-311++G(d,p) basis sets, and a self-consistent reaction-field (SCRF) method was applied to analyze the influence of the solvent. The amino acids investigated can be viewed as constrained phenylalanine analogues with a rigidly oriented aromatic side chain that may interact with the peptide backbone not only sterically but also electronically through the aromatic π orbitals. Their conformational propensities have been found to be strongly influenced by the specific orientation of the aromatic substituent in each stereoisomer and the conformation adopted by the cyclohexane ring, as well as by the environment.
dc.format.extent10 p.
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Spain
dc.subjectÀrees temàtiques de la UPC::Enginyeria química
dc.titleConformational Preferences of 1-Amino-2-phenylcyclohexanecarboxylic Acid, a Phenylalanine Cyclohexane Analogue
dc.contributor.groupUniversitat Politècnica de Catalunya. IMEM - Innovació, Modelització i Enginyeria en (BIO) Materials
dc.description.peerreviewedPeer Reviewed
dc.rights.accessRestricted access - publisher's policy
dc.description.versionPostprint (published version)
upcommons.citation.authorAlemán, C.; Jimenez, A.; Cativiela, C.; Nussinov, R.; Casanovas, J.
upcommons.citation.publicationNameJournal of organic chemistry

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