CHEMISTRY GLOSSARY

glycoside    →   glikozid

Glycoside is one of a group of organic compounds in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. The sugar group is known as the glycon and the non-sugar group as the aglycon. According to the IUPAC definition, all disaccharides and polysaccharides are glycosides where the aglycone is another sugar.

In the free hemiacetal form, sugars will spontaneously equilibrate between the α and β anomers. However, once the glycosidic bond is formed, the anomeric configuration of the ring is locked as either α or β. Therefore, the alpha and beta glycosides are chemically distinct. They will have different chemical, physical, and biological properties. Many glycosides occur abundantly in plants, especially as flower and fruit pigments.

The term glycoside was later extended to cover not only compounds in which the anomeric hydroxy group is replaced by a group -OR, but also those in which the replacing group is -SR (thioglycosides), -SeR (selenoglycosides), -NR1R2 (N-glycosides), or even -CR1R2R3 (C-glycosides). Thioglycoside and selenoglycoside are legitimate generic terms; however the use of N-glycoside, although widespread in biochemical literature, is improper and not recommended here (glycosylamine is a perfectly acceptable term). C-Glycoside is even less acceptable. All other glycosides are hydrolysable; the C-C bond of C-glycosides is usually not. The use and propagation of names based on C-glycoside terminology is therefore strongly discouraged.

glycosyl group    →   glikozidna skupina

The structure obtained by removing the hydroxy group from the hemiacetal function of a monosaccharide.

glycosidic bond    →   glikozidna veza

Glycosidic bond ia a bond between the glycosyl group, the structure obtained by removing the hydroxy group from the hemiacetal function of a monosaccharide, and the -OR group (which itself may be derived from a saccharide and chalcogen replacements thereof (RS–, RSe–). The terms N-glycosides and C-glycosides are misnomers and should not be used. The glycosidic bond can be α or β in orientation, depending on whether the anomeric hydroxyl group was α or β before the glycosidic bond was formed and on the specificity of the enzymatic reaction catalyzing their formation. Once the glycosidic bond is formed, the anomeric configuration of the ring is locked as either α or β. Specific glycosidic bonds therefore may be designated α(1→4), β(1→4), α(1→6), and so on. Cellulose is formed of glucose molecules linked by β(1→4)-glycosidic bonds, whereas starch is composed of α(1→4)-glycosidic bonds.

aglycon    →   aglikon

Aglycon (aglycone) is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. The link between the glycon and aglycon is known as glycosidic bond.

beta-glucan    →   beta-glukan

Beta-glucans are are naturally occurring polysaccharides that contain only glucose as structural components, and are linked with β-glycosidic bonds. They is the most known powerful immune stimulant. The most active forms of β-glucans are those comprising D-glucose units with β(1→3) links and with short side-chains of D-glucose attached at the β(1→6) position. These are referred to as beta-1,3/1,6 glucan. They are a major component of soluble dietary fiber, which can be found in cereal grains (oats, barley, wheat), yeast, and certain mushrooms (shiitake, maitake).

carbohydrate    →   ugljikohidrat

Carbohydrates (often called carbs for short) are polyhydroxy aldehydes or ketones, or substances that yield such compounds on hydrolysis. They are also known as saccharides, a term derived from the Latin word saccharum for sugar. Carbohydrates are the most abundant class of compounds in the biological world, making up more than 50 % of the dry weight of the Earth’s biomass. Every type of food we eat can have its energy traced back to a plant. Plants use carbon dioxide and water to make glucose, a simple sugar, in photosynthesis. Other carbohydrates such as cellulose and starch are made from the glucose. Light from the sun is absorbed by chlorophyll and this is converted to the energy necessary to biosynthesize carbohydrates

The term carbohydrate was applied originally to monosaccharides, in recognition of the fact that their empirical composition can be expressed as C_x(H₂O)_y. Later structural studies revealed that these compounds were not hydrates but the term carbohydrate persists.

Carbohydrates are generally classed as either simple or complex. Simple sugars, or monosaccharides, are carbohydrates that can’t be converted into smaller subunits by hydrolysis. Complex carbohydrates are made of two (disaccharides) or more (oligosaccharides, polysaccharides) simple sugars linked together by acetal (glycosidic) bonds and can be split into the former by hydrolysis.

maltose    →   maltoza

Maltose (malt sugar) is a disaccharide which is obtained with hydrolytic decomposition of starch in the presence of enzyme amylase. Maltose is composed of two glucose molecules linked by an α(1→4)-glycosidic linkage. Maltose has an alpha acetal.

oligosaccharide    →   oligosaharid

Oligosaccharides are carbohydrates containing from three to ten monosaccharide units, each joined to the next by a glycoside bond.

cellulose    →   celuloza

Cellulose, (C₆H₁₀O₅)_n, is a polysaccharide that consists of a long unbranched chain of glucose units linked by (1→4)-β-glycoside bonds. Nature uses cellulose primarily as a structural material to impart strength and rigidity to plants. Leaves, grasses, and cotton are primarily cellulose. The fibrous nature of extracted cellulose has led to its use in textile industry for the production of cotton, artificial silk, etc. Cellulose also serves as raw material for the manufacture of cellulose acetate, known commercially as acetate rayon, and cellulose nitrate, known as guncotton. Gunncotton is the major ingredient in smokeless powder, the explosive propellant used in artillery shells and in ammunition for firearms.

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.