Fitz, D., Reiner, H., Plankensteiner, K., and Rode, B. M. (2007). Possible origins of biohomochirality. Current Chemical Biology, 1:41–52. Plankensteiner, K., Reiner, H.,

and Rode, B. M. (2005). Stereoselective differentiation in the Salt-induced Peptide Formation reaction and its relevance for the origin of life. Peptides, 26:535–541. Plankensteiner, K., Righi, A., Rode, learn more B. M., Gargallo, R., Jaumot, J., and Tauler, R. (2004). Indications towards a stereoselectivity of the salt-induced peptide formation reaction. Inorganice Chimica Acta, 357:649–656. E-mail: Daniel.​Fitz@uibk.​ac.​at Chiral Crystals of Achiral Biological Compounds as an Origin of Homochirality of Biomolecules in Conjunction with Asymmetric Autocatalysis Tsuneomi GS1101 Kawasaki1, Kenta Suzuki1, Yuko Hakoda1, Kunihiko Hatase1, Yuuki Harada1, Nicola Florini2, Gyula Pályi2, Kenso Soai1* 1Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162–8601, Japan; 2Department of Chemistry, University of Modena and Reggio Emilia, via G Campi,

183–41100 Modena, Italy The homochirality of biomolecules such as L-amino acids and D-sugars is one of the essential features of life and has been a puzzle for the chemical origin of life. It is known that some achiral organic compounds crystallize in chiral forms and which has been an important candidate for the origin of chirality. Considering the significant enantioenrichments in biological system, chirality of these crystals should be transferred to other organic compounds with amplification of the quantity and enantioenrichment in the prebiotic world. We previously reported the asymmetric reaction mediated

by chiral organic crystal Arachidonate 15-lipoxygenase as chiral initiators. The chiral crystals serve as chiral initiators of asymmetric autocatalysis (Soai and Kawasaki 2006) and the quantity of chirality has been significantly amplified to achieve the large amount of highly enantioenriched compound (Kawasaki, et al. 2005). In this presentation, we show that cytosine, a prebiotic achiral biomolecule and a nucleobase, spontaneously forms enantioenriched crystals by stirred crystallizations, and the crystal of cytosine acts as a chiral initiator for asymmetric autocatalysis, providing a near enantiopure pyrimidyl alkanol (Kawasaki, et al. 2008). The enantiomorphous one-component single crystals of hippuric acid (N-benzoylglycine), which is an achiral naturally occurring amino acid derivative, also acts as the source of chirality in asymmetric autocatalysis (Kawasaki, et al. 2006). To expand the utility of chiral crystal formed from achiral organic compound for the origin of chirality in asymmetric autocatalysis, we subjected the chiral crystals of benzil and its derivative to the autocatalytic reaction. These results are also discussed. Kawasaki, T., Jo, K., Igarashi, H., Sato, I., Nagano, M., Koshima, H., and Soai, K. (2005).