α-D,L-Sorbose

Abstract

The racemic title compound, C 6 H 12 O 6 , consisting of C-4 epimers of psicose, was crystallized from an aqueous solution of an equimolar mixture of d-and l-sorboses. It was confirmed that d-sorbose (or l-sorbose) formed -pyranose with a Structure description d-and l-sorboses are classified as rare sugars. l-Sorbose is the first l-form hexose found in nature (Nordenson et al., 1979). In this study, we aimed to create a racemic single crystal including both d-and l-sorbose in a 1:1 ratio. There are two independent sorbose molecules, A and B, in the asymmetric unit (Fig. 1). Therefore, there are a total of eight sorbose molecules (four l-and four d-forms) in the unit cell. In the crystal, the d-and l-sorbose molecules are linked weakly, as well as the strong homo-chiral d-d (and l-l) links, via O-HÁ Á ÁO hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2). The crystal structure of the title compound with two independent molecules in the asymmetric unit in space group

Sugar binding of sodium–glucose cotransporters analyzed by voltage-clamp fluorometry

“…However, D-fructose is known to be in equilibrium between the furanose and pyranose states in aqueous solution, with 71% D-fructopyranose, 28% D-fructofuranose, and 1% ketofructose ( 35 ). L-sorbose is a ketohexose-like D-fructose that exhibits the pyranose structure (L-sorbopyranose) at a proportion of more than 98% in aqueous solution ( 36 , 37 ). L-sorbopyranose differs from D-fructopyranose only in the orientation of one OH group.…”

Ethyl α-L-sorboside

“…Ethyl l-sorboside, -sorbopyranoside form, was prepared by Fischer glycosidation from l-sorbose and ethanol (Taguchi et al, 2018). The Fisher method produces isomers such as -, -, and furanose.…”