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Achiral Nucleobase Cytosine Acts as an Origin of Homochirality of Biomolecules in Conjunction with Asymmetric Autocatalysis


  • This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology and by Merck Research Laboratories.


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Crystals to add chirality: Cytosine, a prebiotic achiral biomolecule and an essential nucleobase, spontaneously forms enantioenriched crystals if stirring is applied during crystallization. The chiral crystal of achiral cytosine is a chiral initiator for asymmetric autocatalysis of a pyrimidyl alkanol with amplification of the ee value, which provides a nearly enantiopure alcohol with an absolute configuration correlated to that of the cytosine crystal.