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Crystal structure of β-d,l-psicose

The title compound, C(6)H(12)O(6), a C-3 position epimer of fructose, was crystallized from an aqueous solution of equimolar mixture of d- and l-psicose (1,3,4,5,6-penta­hydroxy­hexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that d-psicose (or l-psicose) formed β-pyran­ose with a (2)...

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Autores principales: Ishii, Tomohiko, Sakane, Genta, Yoshihara, Akihide, Fukada, Kazuhiro, Senoo, Tatsuya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420085/
https://www.ncbi.nlm.nih.gov/pubmed/25995909
http://dx.doi.org/10.1107/S2056989015006623
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author Ishii, Tomohiko
Sakane, Genta
Yoshihara, Akihide
Fukada, Kazuhiro
Senoo, Tatsuya
author_facet Ishii, Tomohiko
Sakane, Genta
Yoshihara, Akihide
Fukada, Kazuhiro
Senoo, Tatsuya
author_sort Ishii, Tomohiko
collection PubMed
description The title compound, C(6)H(12)O(6), a C-3 position epimer of fructose, was crystallized from an aqueous solution of equimolar mixture of d- and l-psicose (1,3,4,5,6-penta­hydroxy­hexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that d-psicose (or l-psicose) formed β-pyran­ose with a (2) C (5) (or (5) C (2)) conformation. In the crystal, an O—H⋯O hydrogen bond between the hy­droxy groups at the C-3 and C-2 positions connects homochiral mol­ecules into a column along the b axis. The columns are linked by other O—H⋯O hydrogen bonds between d- and l-psicose mol­ecules, forming a three-dimensional network. An intra­molecular O—H⋯O hydrogen bond is also observed. The cell volume of racemic β-d,l-psicose [763.21 (6) Å(3)] is almost the same as that of chiral β-d-psicose [753.06 Å(3)].
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spelling pubmed-44200852015-05-20 Crystal structure of β-d,l-psicose Ishii, Tomohiko Sakane, Genta Yoshihara, Akihide Fukada, Kazuhiro Senoo, Tatsuya Acta Crystallogr E Crystallogr Commun Data Reports The title compound, C(6)H(12)O(6), a C-3 position epimer of fructose, was crystallized from an aqueous solution of equimolar mixture of d- and l-psicose (1,3,4,5,6-penta­hydroxy­hexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that d-psicose (or l-psicose) formed β-pyran­ose with a (2) C (5) (or (5) C (2)) conformation. In the crystal, an O—H⋯O hydrogen bond between the hy­droxy groups at the C-3 and C-2 positions connects homochiral mol­ecules into a column along the b axis. The columns are linked by other O—H⋯O hydrogen bonds between d- and l-psicose mol­ecules, forming a three-dimensional network. An intra­molecular O—H⋯O hydrogen bond is also observed. The cell volume of racemic β-d,l-psicose [763.21 (6) Å(3)] is almost the same as that of chiral β-d-psicose [753.06 Å(3)]. International Union of Crystallography 2015-04-09 /pmc/articles/PMC4420085/ /pubmed/25995909 http://dx.doi.org/10.1107/S2056989015006623 Text en © Ishii et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Data Reports
Ishii, Tomohiko
Sakane, Genta
Yoshihara, Akihide
Fukada, Kazuhiro
Senoo, Tatsuya
Crystal structure of β-d,l-psicose
title Crystal structure of β-d,l-psicose
title_full Crystal structure of β-d,l-psicose
title_fullStr Crystal structure of β-d,l-psicose
title_full_unstemmed Crystal structure of β-d,l-psicose
title_short Crystal structure of β-d,l-psicose
title_sort crystal structure of β-d,l-psicose
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420085/
https://www.ncbi.nlm.nih.gov/pubmed/25995909
http://dx.doi.org/10.1107/S2056989015006623
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