Origin of Homochirality of Amino Acids in the Biosphere 英文参考文献.docVIP

Symmetry 2010, 2, 1022-1032; doi:10.3390/sym2021022 OPEN ACCESS symmetry ISSN 2073-8994 /journal/symmetry Review Origin of Homochirality of Amino Acids in the Biosphere Shosuke Kojo Department of Food Science and Nutrition, Nara Women’s University, Nara 630-8506 Japan; E-Mail: kojo@cc.nara-wu.ac.jp Received: 21 January 2010; in revised form: 28 April 2010/ Accepted: 10 May 2010 / Published: 13 May 2010 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 1. Introduction Explanation of the homochirality of amino acids in the biosphere is one of the most important mysteries in the origin of life [1,2]. According to the long history of asymmetric synthesis, it is considered that absolute asymmetric synthesis, namely asymmetric synthesis without the aid of an asymmetric molecule as a reactant or catalyst, is imposs