Reducing sugar

A reducing sugar is any sugar that is capable of acting as a reducing agent because it has a free aldehyde group or a free ketone group. All monosaccharides are reducing sugars, along with some disaccharides, oligosaccharides, and polysaccharides. The monosaccharides can be divided into two groups: the aldoses, which have an aldehyde group, and the ketoses, which have a ketone group. Ketoses must first tautomerize to aldoses before they can act as reducing sugars. The common dietary monosaccharides galactose, glucose and fructose are all reducing sugars. A reducing sugar is any sugar that is capable of acting as a reducing agent because it has a free aldehyde group or a free ketone group. All monosaccharides are reducing sugars, along with some disaccharides, oligosaccharides, and polysaccharides. The monosaccharides can be divided into two groups: the aldoses, which have an aldehyde group, and the ketoses, which have a ketone group. Ketoses must first tautomerize to aldoses before they can act as reducing sugars. The common dietary monosaccharides galactose, glucose and fructose are all reducing sugars. Disaccharides are formed from two monosaccharides and can be classified as either reducing or nonreducing. Nonreducing disaccharides like sucrose and trehalose have glycosidic bonds between their anomeric carbons and thus cannot convert to an open-chain form with an aldehyde group; they are stuck in the cyclic form. Reducing disaccharides like lactose and maltose have only one of their two anomeric carbons involved in the glycosidic bond, meaning that they can convert to an open-chain form with an aldehyde group. The aldehyde functional group allows the sugar to act as a reducing agent, for example in the Tollens' test or Benedict's test. The cyclic hemiacetal forms of aldoses can open to reveal an aldehyde and certain ketoses can undergo tautomerization to become aldoses. However, acetals, including those found in polysaccharide linkages, cannot easily become free aldehydes. Reducing sugars react with amino acids in the Maillard reaction, a series of reactions that occurs while cooking food at high temperatures and that is important in determining the flavor of food. Also, the levels of reducing sugars in wine, juice, and sugarcane are indicative of the quality of these food products. A reducing sugar is one that reduces another compound and is itself oxidized; that is, the carbonyl carbon of the sugar is oxidized to a carboxyl group. A sugar is classified as a reducing sugar only if it has an open-chain form with an aldehyde group or a free hemiacetal group. Monosaccharides which contain an aldehyde group are known as aldoses, and those with a ketone group are known as ketoses. The aldehyde can be oxidized via a redox reaction in which another compound is reduced. Thus, a reducing sugar is one that reduces certain chemicals. Sugars with ketone groups in their open chain form are capable of isomerizing via a series of tautomeric shifts to produce an aldehyde group in solution. Therefore, ketone-bearing sugars like fructose are considered reducing sugars but it is the isomer containing an aldehyde group which is reducing since ketones cannot be oxidized without decomposition of the sugar. This type of isomerization is catalyzed by the base present in solutions which test for the presence of aldehydes. Aldoses or aldehyde-bearing sugars are also reducing because during oxidation of aldoses, there are certain oxidizing agents that are reduced. The reducing end of a disaccharide is the monosaccharide with a free anomeric carbon that is not involved in a glycosidic bond and is thus capable of converting to the open-chain form. Recall that disaccharides consist of two monosaccharides and may be either reducing or nonreducing. However, even a reducing disaccharide will only have one reducing end, as disaccharides are held together by glycosidic bonds, which consist of at least one anomeric carbon. With one anomeric carbon unable to convert to the open-chain form, only the free anomeric carbon is available to reduce another compound. A nonreducing disaccharide has both anomeric carbons tied up in the glycosidic bond.