Generation of Absolute Controlled Crystal Chirality by the Removal of Crystal Water from Achiral Crystal of Nucleobase Cytosine

Kawasaki, Tsuneomi; Hakoda, Yuko; Mineki, Hiroko; Suzuki, Kenta; Soai, Kenso

doi:10.1021/ja1000938

Cited by 65Crystallization and Solubility StudiesCrystallography and molecular interactionsCrystal structures of chemical compounds

Generation of Absolute Controlled Crystal Chirality by the Removal of Crystal Water from Achiral Crystal of Nucleobase Cytosine

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Kawasaki, Tsuneomi, Hakoda, Yuko, Mineki, Hiroko, Suzuki, Kenta, Soai, Kenso·2010·Journal of the American Chemical Society

DOI 10.1021/ja1000938PMC PMC2831480

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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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The chirality of the dehydrated cytosine crystal is correlated with the enantiotopic face of the achiral cytosine monohydrate crystal.
“The chirality of the formed dehydrated cytosine crystal is correlated with the enantiotopic face of the achiral cytosine monohydrate crystal.”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [81]
Heating one enantiotopic face of an achiral cytosine monohydrate crystal removes crystal water and gives a chiral dehydrated cytosine crystal.
“It was found that the elimination of the crystal water by heating one of the enantiotopic faces of an achiral crystal of cytosine monohydrate affords a chiral crystal of dehydrated cytosine.81)”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [81]

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Authors: Kawasaki, T., Hakoda, Y., Mineki, H., Suzuki, K., & Soai, K.
Affiliations: Tokyo University of Science (JP)
Corresponding author: Soai, Kenso
ORCID: Kawasaki, Tsuneomi
Soai, Kenso
Venue: Journal of the American Chemical Society
Publisher: American Chemical Society (ACS)
Published: 2010-02-12
Volume: 132
Issue: 9
Pages: 2874-2875
ISSN: 0002-7863 (ISSN-L)
1520-5126
DOI: 10.1021/ja1000938
PMC: PMC2831480
OpenAlex: W2032638412
Cited by: 65
References: 35
Citations by year: 2025: 1 · 2023: 3 · 2022: 9 · 2021: 5 · 2020: 2 · 2019: 4 · 2018: 1 · 2017: 6 · 2016: 7 · 2015: 4 · 2014: 3 · 2013: 5 · 2012: 7
FWCI: 3.14
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: other-oa
pubs.acs.org/page/policy/authorchoice_termsofuse.html (vor)
Locations: Journal of the American Chemical Society (publishedVersion, other-oa)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Funders: Japan Society for the Promotion of Science
Topics: Physical Sciences › Materials Science › Materials Chemistry › Crystallization and Solubility Studies
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Crystallography and molecular interactions
Physical Sciences › Chemistry › Inorganic Chemistry › Crystal structures of chemical compounds
Keywords: crystal chirality, enantioselective crystallization, nucleobases
MeSH terms: Crystallization, Cytosine, Hydrogen Bonding, Models, Molecular, Stereoisomerism, Water, Molecular Structure

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Generation of Absolute Controlled Crystal Chirality by the Removal of Crystal Water from Achiral Crystal of Nucleobase Cytosine

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