Crystal structure of β-D,L-psicose

Tomohiko Ishii; Genta Sakane; Akihide Yoshihara; Kazuhiro Fukada; Tatsuya Senoo; H. Ishida

doi:10.1107/S2056989015006623

Crystal structure of β-D,L-psicose

Tomohiko Ishii, Genta Sakane, Akihide Yoshihara, Kazuhiro Fukada, Tatsuya Senoo, H. Ishida

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The title compound, C₆H₁₂O₆, 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-penta-hydroxyhexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that D-psicose (or L-psicose) formed β-pyranose with a²C₅ (or⁵C₂) 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) Å³] is almost the same as that of chiral β-D-psicose [753.06 Å³].

Original language	English
Pages (from-to)	o289-o290
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	5
DOIs	https://doi.org/10.1107/S2056989015006623
Publication status	Published - May 1 2015

Keywords

Crystal structure
Hydrogen bonding
Racemic compound
Rare sugar

ASJC Scopus subject areas

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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title = "Crystal structure of β-D,L-psicose",

abstract = "The title compound, C6H12O6, 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-penta-hydroxyhexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that D-psicose (or L-psicose) formed β-pyranose with a2C5 (or5C2) 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) {\AA}3] is almost the same as that of chiral β-D-psicose [753.06 {\AA}3].",

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T1 - Crystal structure of β-D,L-psicose

AU - Ishii, Tomohiko

AU - Sakane, Genta

AU - Yoshihara, Akihide

AU - Fukada, Kazuhiro

AU - Senoo, Tatsuya

AU - Ishida, H.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - The title compound, C6H12O6, 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-penta-hydroxyhexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that D-psicose (or L-psicose) formed β-pyranose with a2C5 (or5C2) 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) Å3] is almost the same as that of chiral β-D-psicose [753.06 Å3].

AB - The title compound, C6H12O6, 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-penta-hydroxyhexan-2-one, ribo-2-hexulose, allulose), and it was confirmed that D-psicose (or L-psicose) formed β-pyranose with a2C5 (or5C2) 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) Å3] is almost the same as that of chiral β-D-psicose [753.06 Å3].

KW - Crystal structure

KW - Hydrogen bonding

KW - Racemic compound

KW - Rare sugar

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Crystal structure of β-D,L-psicose

Abstract

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