Cyclic structure of Fructose

Like glucose, fructose also has a cyclic structure. Since fructose contains a keto group, it forms an intramolecular hemiketal. In the hemiketal formation, C5– OH of the fructose combines with C2-keto group. As a result, C2 becomes chiral and thus has two possible arrangements of CH2OH and OH group around it. Thus, D-fructose exists in two stereoisomeric forms, i.e., α-D-fructopyranose and β-D fructopyranose. However in the combined state (such as sucrose), fructose exists in furanose form as shown below:


The two stereoisomeric forms of glucose, i.e., α-D-glucose and β-D-glucose exist in separate crystalline forms and thus have different melting points and specific roations. For example α-D-glucose has a m.p. of 419 K with a specific rotation of +112° while  β-D-glucose has a m.p. of 424 K and has a specific rotation of +19°. However, when either of these two forms is dissolved in water and allowed to stand, it gets converted into an equilibrium mixture of α-and β-forms through a small amount of the open chain form.

As a result of this equilibrium, the specific rotation of a freshly prepared solution of α-D-glucose gradually decreases from of +112° to +52.7° and that of β-D-glucose gradually increases from +19° to +52.7°.

This change in specific rotation of an optically active compound in solution with time, to an equilibrium value, is called mutarotation. During mutarotation, the ring opens and then recloses either in the inverted position or in the original position giving a mixture of α-and-β-forms. All reducing carbohydrates, i.e., monosaccharides and disacchardies (maltose, lactose etc.) undergo mutarotation in aqueous solution.

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