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Closed Access item Conformational analysis of a cyclopropane analogue of phenylalanine with two geminal phenyl substituents

Authors:Casanovas, Jordi
Jiménez, Ana I.
Cativiela, Carlos
Pérez, Juan J.
Alemán, Carlos
Issue Date:22-Feb-2006
Publisher:American Chemical Society
Citation:The Journal of Physical Chemistry B 110(11): 5762–5766 (2006)
Abstract:Quantum mechanical methods have been used to investigate the intrinsic conformational preferences of 1-amino-2,2-diphenylcyclopropanecarboxylic acid (c3Dip), a cyclopropane analogue of phenylalanine bearing two phenyl substituents on the same β-carbon. Geometries, energies, and frequencies were calculated on the N-acetyl-N‘-methylamide derivative at the HF and B3LYP levels using the 6-31G(d), 6-311G(d), and 6-31+G(d,p) basis sets. Four minimum energy conformations were characterized: axial C7, equatorial C7, right-handed helix, and polyproline II. Analysis of the whole results, which are fully consistent with available experimental data, indicates that c3Dip tends to promote γ-turn conformations.
Description:5 pages, 3 figures, 4 tables.
Publisher version (URL):http://dx.doi.org/10.1021/jp0542569
Appears in Collections:(ICMA) Artículos

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