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Chiroptical Properties of Amino Acids: A Density Functional Theory Study
Laboratoire de Chimie des Molécules Bioactives et des Arômes UMR 6001 CNRS-UNSA, Université de Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice, France
Institute for Applied and Physical Chemistry, University of Bremen, Leobener Str. NW2, 28359 Bremen, Germany
Institute for Storage Ring Facilities, Aarhus University, Ny Munkegade 120, DK-8000 Aarhus C, Denmark
* Author to whom correspondence should be addressed.
Received: 6 March 2010; in revised form: 6 April 2010 / Accepted: 14 April 2010 / Published: 19 April 2010
Abstract: Amino acids are involved in many scientific theories elucidating possible origins of life on Earth. One of the challenges when discussing the evolutionary origin of biopolymers such as proteins and oligonucleotides in living organisms is the phenomenon that these polymers implement monomers of exclusively one handedness, a feature called biomolecular homochirality. Many attempts have been made to understand this process of racemic symmetry breaking. Assuming an extraterrestrial origin of the molecular building blocks of living organisms, their susceptibility to asymmetric photolysis by the absorption of circularly polarized electromagnetic radiation in interstellar space was proposed. In order to predict whether the interaction of circularly polarized light with various racemic amino acids can induce an enantiomeric excess, we investigated the electronic and chiroptical properties of the amino acids valine and isovaline by a molecular modelling approach based on quantum chemistry (Density Functional Theory). The average spectra of both L-valine and L-isovaline have been produced on the basis of Boltzmann population analysis using computed spectra for the various conformations of each amino acid.
Keywords: amino acids; homochirality; circular dichroism; ab initio calculations; DFT; Boltzman population analysis
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Adrian-Scotto, M.; Antonczak, S.; Bredehöft, J.H.; Hoffmann, S.V.; Meierhenrich, U.J. Chiroptical Properties of Amino Acids: A Density Functional Theory Study. Symmetry 2010, 2, 935-949.
Adrian-Scotto M, Antonczak S, Bredehöft JH, Hoffmann SV, Meierhenrich UJ. Chiroptical Properties of Amino Acids: A Density Functional Theory Study. Symmetry. 2010; 2(2):935-949.
Adrian-Scotto, Martine; Antonczak, Serge; Bredehöft, Jan Hendrik; Hoffmann, Søren V.; Meierhenrich, Uwe J. 2010. "Chiroptical Properties of Amino Acids: A Density Functional Theory Study." Symmetry 2, no. 2: 935-949.