CHEMISTRY GLOSSARY

mutarotation    →   mutarotacija

Mutarotation is the change in optical rotation accompanying epimerization. In carbohydrate chemistry this term usually refers to epimerization at the hemiacetal carbon atom. In general α- and β-form are stable solids, but in solution they rapidly equilibrate. For example, D-glucose exists in an equilibrium mixture of 36 % α-D-glucopyranose and 64 % β-D-glucopyranose, with only a tiny fraction in the open-chain form. The equilibration occurs via the ring opening of the cyclic sugar at the anomeric center with the acyclic form as the intermediate. Mutarotation was discovered by French chemist Augustin-Pierre Dubrunfaut (1797-1881) in 1846.

disaccharide    →   disaharid

Disaccharides are compounds in which two monosaccharides are joined by a glycosidic bond. A glycosidic bond to the anomeric carbon can be either α or β. For example, maltose, the disaccharide obtained by enzyme-catalyzed hydrolysis of starch, consists of two D-glucopyranose units joined by a 1,4’-α-glycoside bond. The "prime" superscript indicates that C-4 is not in the same ring as C-1. Unlike the other disaccharides, sucrose is not a reducing sugar and does not exhibit mutarotation because the glycosidic bond is between the anomeric carbon of glucose and the anomeric carbon of fructose.

lactose    →   laktoza

Lactose (milk sugar) is a disaccharide comprising one glucose molecule linked to a galactose molecule by an β(1→4)-glycosidic linkage. Lactose has a beta acetal. Lactose is manufactured by the mammary gland and occurs only in milk (from 4 % to 7 %). Lactose intolerance is a common medical condition that results in diarrhea, abdominal pain, and flatulence and is caused by reduced or absent activity of enzyme lactase.

Like cellobiose and maltose, lactose is a reducing sugar. All reducing sugar undergo mutarotation in aqueous solution. The equilibrium mixture at 20 °C is composed of 62.7 % β-lactose (β-D-galactopyranosyl-(1→4)-β-D-glucopyranose) and 37.3 % α-lactose (β-D-galactopyranosyl-(1→4)-α-D-glucopyranose).

polysaccharide    →   polisaharid

Polysaccharides are compounds consisting of a large number of simple sugars (monosaccharides) linked together by glycosidic bonds. When polysaccharides are composed of a single monosaccharide building block, they are termed homopolysaccharides. Heteropolysaccharides contain two or more different types of monosaccharide. Polysaccharides may have molecular weights of up to several million and are often highly branched. Since they have only the one free anomeric -OH group at the end of a very long chain, polysaccharides aren’t reducing sugars and don’t show noticeable mutarotation. The most common polysaccharides are cellulose, starch, and glycogen.

sucrose    →   saharoza

Sucrose (saccharose), or ordinary table sugar, is a disaccharide in which α-D-glucopyranose and β-D-fructofuranose are joined at their anomeric carbons by a glycosidic bond. There are no hemiacetals remaining in the sucrose and therefore sucrose is not a reducing sugar and does not exhibit mutarotation. Sugar is a white crystalline sweet compound found in many plants and extracted from sugar cane and sugar beet. It is used as a sweetening agent in food and drinks. If heated to 200 °C, sucrose becomes caramel. When sucrose is hydrolyzed it forms an equimolar mixture of glucose and fructose. This mixture of monosaccharides is called invert sugar. Honeybees have enzymes called invertases that catalyze the hydrolysis of sucrose. Honey, in fact, is primarily a mixture of glucose, fructose, and sucrose.