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Chiroptical Properties of Amino Acids: A Density Functional Theory Study
Symmetry 2010, 2(2), 1022-1032; doi:10.3390/sym2021022
Review

Origin of Homochirality of Amino Acids in the Biosphere

Received: 21 January 2010 / Revised: 28 April 2010 / Accepted: 10 May 2010 / Published: 13 May 2010
(This article belongs to the Special Issue Symmetry of Life and Homochirality)
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Abstract

Discussions are made concerning realistic mechanisms for the origin of L-amino acids in the biosphere. As the most plausible mechanism, it is proposed that a mixture of racemic amino acids in the prebiotic sea caused spontaneous and effective optical resolution through self crystallization, even if asymmetric synthesis of a single amino acid has never occurred without the aid of an optically active molecule. This hypothesis is based on recrystallization of a mixture of D,L-amino acids in the presence of excess of D,L-asparagine (Asn). The enantiomeric excess (ee) of each amino acid in the resulting crystals indicates that crystallization of co-existing amino acids with the configuration same as that of Asn took place, although it was incidental whether the enrichment occurred in L- or D-amino acids. In addition, the resulting ee was sufficiently high (up to 100%) to account for the predominance of L-amino acids on the earth.
Keywords: homochirality; L-amino acid; crystallization; chemical evolution; optical resolution; asymmetric synthesis; enantiomeric excess homochirality; L-amino acid; crystallization; chemical evolution; optical resolution; asymmetric synthesis; enantiomeric excess
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kojo, S. Origin of Homochirality of Amino Acids in the Biosphere. Symmetry 2010, 2, 1022-1032.

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