CHEMISTRY GLOSSARY

monosaccharide    →   monosaharid

Monosaccharides are carbohydrates, with the general formula C_n(H₂O)_n, that cannot be decomposed to a simpler carbohydrates by hydrolysis.

Depending on whether the molecule contains an aldehyde group (-CHO) or a ketone group (-CO-) monosaccharide can be a polyhydroxy aldehyde (aldose) or a polyhydroxy ketone (ketose). These aldehyde and ketone groups confer reduction properties on monosaccharides. They are also classified according to the number of carbon atoms they contain: trioses have three carbon atoms, tetroses four, pentoses five, hexoses six, heptoses seven, etc. These two systems of classification are often combined. For example, a six-carbon polyhydroxy aldehyde such as D-glucose is an aldohexose, whereas a six-carbon polyhydroxy ketone such as D-fructose is a ketohexose.

The notations D and L are used to describe the configurations of carbohydrates. In Fischer projections of monosaccharides, the carbonyl group is always placed on top (in the case of aldoses) or as close to the top as possible (in the case of ketoses). If the OH group attached to the bottom-most asymmetric carbon (the carbon that is second from the bottom) is on the right, then the compound is a D-sugar. If the OH group is on the left, then the compound is an L-sugar. Almost all sugars found in nature are D-sugars.

Monosaccharides can exist as either straight-chain or ring-shaped molecules. During the conversion from straight-chain form to cyclic form, the carbon atom containing the carbonyl oxygen, called the anomeric carbon, becomes a chiral center with two possible configurations (anomers), α and β. When the stereochemistry of the first carbon matches the stereochemistry of the last stereogenic center the sugar is the α-anomer when they are opposite the sugar is the β-anomer.

anomer    →   anomer

Anomers are diastereoisomers of cyclic forms of sugars or similar molecules differing in the configuration at the anomeric carbon (C-1 atom of an aldose or the C-2 atom of a 2-ketose). The cyclic forms of carbohydrates can exist in two forms, α- and β- based on the position of the substituent at the anomeric center. Anomer are designated α if the configuration at the anomeric carbon is the same as that at the reference asymmetric carbon in a Fischer projection. If the configuration differs the anomer is designated β. For example, α-D-glucopyranose and β-D-glucopyranose, the two cyclic forms of glucose, are anomers.

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.

glycosyl group    →   glikozidna skupina

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

ketose    →   ketoze

Ketose is any monosaccharide sugar that contains a ketone (carbonyl) group.

oligosaccharide    →   oligosaharid

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

pentose    →   pentoza

Pentose is a monosaccharide with five carbon atoms in its chain.

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.

glucose    →   glukoza

Glucose (grape sugar, blood sugar), C₆H₁₂O₆, is an aldohexose (a monosaccharide sugar having six carbon atoms and an aldehyde group). An older common name for glucose is dextrose, after its dextrorotatory property of rotating plane polarized light to the right. Glucose in free (in sweet fruits and honey) or combined form (sucrose, starch, cellulose, glycogen) is is probably the most abundant organic compound in nature. During the photosynthesis process, plants use energy from the sun, water from the soil and carbon dioxide gas from the air to make glucose. In cellular respiration, glucose is ultimately broken down to yield carbon dioxide and water, and the energy from this process is stored as ATP molecules (36 molecules of ATP across all processes).

Naturally occurring glucose is D isomers (OH group on the stereogenic carbon farthest from the aldehyde group, C-5, is to the right in the Fischer projection). Although often displayed as an open chain structure, glucose and most common sugars exist as ring structures. In the α form, the hydroxyl group attached to C-1 and the CH₂OH attached to C-5 are located on opposite sides of the ring. β-glucose has these two groups on the same side of the ring. The full names for these two anomers of glucose are α-D-glucopyranose and β-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.