betaDfructofuranoside

Beta-D-fructofuranoside refers to a family of glycosides in which a beta-D-fructofuranose unit forms the sugar part of the molecule. In these compounds, the anomeric carbon of the fructose furanose ring (C-2 in the five-membered ring) is linked to an aglycone or substituent via a glycosidic bond. The designation beta indicates the configuration of the glycosidic bond at the anomeric position, with the substituent oriented in the beta position. The corresponding counterpart is the alpha-D-fructofuranoside.

Common examples in chemical literature include methyl beta-D-fructofuranoside and ethyl beta-D-fructofuranoside, among others where various alcohols or aglycones are attached to the fructofuranoside as the glycosyl donor. In naming, the term highlights the fructose-derived sugar moiety and its beta anomeric linkage.

Chemical and biological relevance: beta-D-fructofuranosides are used as synthetic intermediates and protective forms in carbohydrate chemistry, and they serve as substrates in studies of glycosidases and enzymatic hydrolysis. Hydrolysis of a beta-D-fructofuranoside cleaves the glycosidic bond to yield the aglycone and D-fructose. The beta configuration can influence hydrolysis rate and enzyme specificity compared with alpha-fructofuranosides or other sugar glycosides.

See also: alpha-D-fructofuranoside, methyl beta-D-fructofuranoside, fructosides.