Fructose hemiketal form, structure

Monosaccharide structures may be depicted in open-chain forms showing their carbonyl character, or in cyclic hemiacetal or hemiketal forms. Alongside the Fischer projections of glucose, ribose, and fructose shown earlier, we included an alternative... 

In a similar manner, ketones can react with alcohols to form hemiketals. The analogous intramolecular reaction of a ketose sugar such as fructose yields a cyclic hemiketal (Figure 7.6). The five-membered ring thus formed is reminiscent of furan and is referred to as a furanose. The cyclic pyranose and fura-nose forms are the preferred structures for monosaccharides in aqueous solution. At equilibrium, the linear aldehyde or ketone structure is only a minor component of the mixture (generally much less than 1%). 

D-Fructose, a ketohexose, can potentially form either a five-membered (furanose) or a six-membered (pyranose) ring involving formation of an internal hemiketal linkage between C2 (the anomeric carbon atom) and the C5 or C(, hydroxyl group, respectively. The hemiketal linkage introduces a new asymmetrical center at the C2 position. Thus, two anomeric forms of each of the fructo-furanose and fructopyranose ring structures are possible (Figure 9-10). In aqueous solution at equilibrium, fructose is present predominantly in the )3-fructopyranose form. 

Fructose is a ketose, or ketone sugar. Recall that the reaction between an alcohol and a ketone )delds a hemiketal. Thus the reaction between the C-2 keto group and the C-5 hydroxyl group in the fructose molecule produces an intramolecular hemiketal. Fructose forms a five-membered ring structure. 

Ans. The previous discussion was an oversimplification. Hemiketal formation in o-fructose and other ketohexoses results in reaction at both C-5 and C-6 to give a mixture of 5- and 6-membered rings. Pure fructose in solution consists of a mixture of the a- and /3-anomers of both furanose and pyranose structures, as well as a very small amount (< 0.2 percent) of the open-chain form. However, all combined forms of o-fructose, e.g., fructose combined with glucose in sucrose, involve only the 5-membered ring. For this reason, most texts simplify matters for the student by ignoring the pyranose structures. The exclusive use of the 5-membered ring in combined forms of o-fructose is not understood. 

Fructose is a ketohexose sugar. The cyclic structure formed is called a hemiketal, and the five membered ring that is formed is called furanose ring. The straight chain structure and the cyclic structures of fructose are shown in Figure 29-5. 

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