Disaccharide sugars are formed by a condensation reaction between two monosaccharides.

The covalent linkage is called an O-glycosidic bond and represents the formation of an acetal from a hemiacetal and an alcohol. The glycosidic bond in the disaccharide maltose is called anα1-4 linkage because the anomeric carbon is in the αconformation.

The glucose molecule on the right retains the hemiacetal structure at its C-1 anomeric carbon and can convert to the aldehyde open chain form in a reaction involving the reduction of Cu2+ to form Cu+. Using this functional definition (the reduction of Cu2+), the glucose on the right is designated as the reducing end of the disaccharide molecule because it can participate in a reduction reaction. In contrast, the glucose on the left represents the nonreducing end because the C-1 carbon is part of the α1-4 linkage and cannot form the open chain structure in a Cu2+ reduction reaction. Since maltose contains one reducing end it is called a reducing sugar. Disaccharides can contain different monosaccharide units connected through αor βglycosidic bonds involving ring carbons, and therefore, it is convenient to name disaccharides using a descriptive nomenclature. Using standard conventions, the disaccharide is named by first listing the nonreducing monosaccharide on the left, followed by the glycosidic linkage between the two monosaccharides, and then the monosaccharide on the right. With this shorthand nomenclature, maltose can be described as a Glc(α1-4)Glc disaccharide in which the abbreviation "Glc" is used for glucose. There are three common disaccharides found in nature: 1) lactose, also called milk sugar, which contains a β1-4 glycosidic bond linking a galactose (Gal) to a glucose to form Gal(β1-4)Glc, 2) sucrose, made in plants and used as table sugar in its crystalline form, contains fructose (Fru) linked to glucose through the two anomeric carbons to form Glu(α1-β2)Fru, and 3) trehalose, a glucose disaccharide made in insects, contains a glycosidic bond between the two anomeric carbons to form the disaccharide Glc(α1-α1)Glc. Importantly, of these three disaccharides, only lactose is a reducing sugar, because like maltose, it contains a free anomeric carbon that can interconvert the hemiacetal to an aldehyde. Both sucrose and trehalose are nonreducing sugars because they lack a reducing end.

Sign up to vote on this title
UsefulNot useful