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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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Detalles Bibliográficos
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
Descripción
Sumario: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)].