Bulletin of the Chemical Society of Japan p. 1193 - 1197 (2010)
Update date:2022-08-16
Topics:
Fukada, Kazuhiro
Ishii, Tomohiko
Tanaka, Katsushi
Yamaji, Masatsugu
Yamaoka, Yuya
Kobashi, Ken-Ichi
Izumori, Ken
X-ray crystal analysis for D-psicose (C3-position epimer of D-fructose) crystallized from aqueous solution was successfully performed for the first time. It was confirmed that D-psicose crystallized solely as β-D-pyranose with 1C (1C4 (d)) conformation. The crystal system (orthorhombic), space group (#19, P212121), and number of molecules per unit cell (Z = 4) are the same as those for β-D-fructopyranose, α-L-sorbopyranose, and α-D-tagatopyranose. Solubility of D-psicose at 25 °C was 291 g per 100 g water. Mutarotation was further investigated recording the time course of specific rotation [α] at 589 nm after the dissolution of D-psicose in water. It is thought that [α] for β-D-psicopyranose in water may be ca.-85degdm -1g-1 cm3. The time course of absorbance at 280 nm after the dissolution of D-psicose was also measured to see the development of open-chain carbonyl-form in the solution, and the first-order kinetic behavior with the rate constant k = 4.44 ms-1 was confirmed. Assuming the equilibrium content of carbonyl-form of D-psicose as 0.2%, the molar absorption coefficient, ε, for the carbonyl-form was estimated to be 160cm-1 M-1.
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