Enantiodivergent formation of a chiral cytosine crystal by removal of crystal water from an achiral monohydrate crystal under reduced pressure

Autor:	Hiroko Mineki, Yoshiyasu Kaimori, Tsuneomi Kawasaki, Arimasa Matsumoto, Kenso Soai
Rok vydání:	2013
Předmět:	Stereochemistry Organic Chemistry medicine.disease Catalysis law.invention Nucleobase Inorganic Chemistry Crystal Autocatalysis chemistry.chemical_compound Crystallography chemistry law medicine Anhydrous Dehydration Physical and Theoretical Chemistry Crystallization Chirality (chemistry) Cytosine
Zdroj:	Tetrahedron: Asymmetry. 24:1365-1367
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2013.09.020
Popis:	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.
Databáze:	OpenAIRE
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