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. 2010 Mar 10;132(9):2874-5.
doi: 10.1021/ja1000938.

Generation of absolute controlled crystal chirality by the removal of crystal water from achiral crystal of nucleobase cytosine

Tsuneomi Kawasaki  1 , Yuko Hakoda, Hiroko Mineki, Kenta Suzuki, Kenso Soai
Affiliations
Free PMC article

Generation of absolute controlled crystal chirality by the removal of crystal water from achiral crystal of nucleobase cytosine

Tsuneomi Kawasaki et al. J Am Chem Soc. .
Free PMC article

Abstract

The enantioselective formation of chiral crystal of achiral nucleobase cytosine was achieved mediated by the crystal direction selective dehydration of crystal water in the achiral crystal of cytosine monohydrate (P2(1)/c). Heat transfer from the enantiotopic face of the single crystal of cytosine monohydrate afforded the enantiomorphous crystal of anhydrous cytosine.

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Figures

Figure 1
Figure 1
Single crystal of cytosine monohydrate 1·H2O.
Figure 2
Figure 2
Generation of crystal chirality by the removal of crystal water of cytosine monohydrate 1·H2O.
Figure 3
Figure 3
Solid-state properties of cytosine crystals. a: Solid-state CD of anhydrous 1. Lines of the same color indicate the CD signals of the anhydrous crystals that arise from the identical single crystals of 1·H2O. b: X-ray powder diffraction patterns. (a) Cytosine 1 (P212121: simulation from single crystal data). (b) Dehydrated cytosine 1 (observed pattern). (c) Cytosine monohydrate 1·H2O (P21/c: simulation from single crystal data).
Figure 4
Figure 4
Formation of helical H-bond network by the thermal dehydration of crystal water.
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