Abstract
An achiral nucleobase cytosine forms an achiral monohydrate crystal (space group: P21/c) by crystallization from a water solution. It was found that the removal of crystal water under reduced pressure at room temperature afforded a chiral crystal of anhydrous cytosine (P212121). The crystal chirality of anhydrous cytosine corresponds to the enantiotopic crystal face of the achiral monohydrate; therefore, when the enantiotopic b1-face is exposed to the reduced pressure, dehydration occurred in the direction from the b1-face to provide [CD(+)310KBr]-cytosine crystal. In contrast, dehydration from the b2-face gave the opposite enantiomorphous [CD(−)310KBr]-cytosine crystal. The correlation between enantiotopic faces and the formed crystal chirality is opposite to that from dehydration by heating. The formed chiral cytosine crystals act as a chiral trigger for asymmetric autocatalysis with enantioenrichment amplification of pyrimidylalkanol.
Published Version
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