Crystal structure of β-D,L-psicose

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

Research output: Contribution to journalArticle

4 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 languageEnglish
Pages (from-to)o289-o290
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number5
DOIs
Publication statusPublished - May 1 2015

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Hydrogen bonds
Crystal structure
hydrogen bonds
crystal structure
Fructose
Molecules
Conformations
molecules
aqueous solutions
Crystals
cells
crystals
psicose

Keywords

  • Crystal structure
  • Hydrogen bonding
  • Racemic compound
  • Rare sugar

ASJC Scopus subject areas

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

Cite this

Crystal structure of β-D,L-psicose. / Ishii, Tomohiko; Sakane, Genta; Yoshihara, Akihide; Fukada, Kazuhiro; Senoo, Tatsuya; Ishida, Hiroyuki.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 5, 01.05.2015, p. o289-o290.

Research output: Contribution to journalArticle

Ishii, T, Sakane, G, Yoshihara, A, Fukada, K, Senoo, T & Ishida, H 2015, 'Crystal structure of β-D,L-psicose', Acta Crystallographica Section E: Structure Reports Online, vol. 71, no. 5, pp. o289-o290. https://doi.org/10.1107/S2056989015006623
Ishii, Tomohiko ; Sakane, Genta ; Yoshihara, Akihide ; Fukada, Kazuhiro ; Senoo, Tatsuya ; Ishida, Hiroyuki. / Crystal structure of β-D,L-psicose. In: Acta Crystallographica Section E: Structure Reports Online. 2015 ; Vol. 71, No. 5. pp. o289-o290.
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