CHEMISTRY GLOSSARY

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.

hemiacetal    →   poluacetal

Hemiacetals are organic compounds having the general formula R₂C(OH)OR’ (R’ ≠ H), derived from aldehydes or ketones by formal addition of an alcohol to the carbonyl group. Hemiacetals are generally unstable compounds. In some cases however, stable cyclic hemiacetals can be readily formed, especially when 5- and 6-membered rings are possible. In this case an intramolecular OH group reacts with the carbonyl group. Glucose and many other aldoses exist as cyclic hemiacetals whereas fructose and similar ketoses exist as cyclic hemiketals. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H).

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.

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.

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.

oxo compound    →   okso-spoj

Oxo compounds are organic compounds that contain the karbonyl group, C=O. The term thus embraces aldehydes, carboxylic acids, ketones, amides, and esters.

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.

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.

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.

tautomerism    →   tautomerija

Tautomerism refers to equilibrium between two different structures of the same compound. Usually the tautomers differ in the point of attachment of a hydrogen atom. One of the most common examples of a tautomeric system is the equilibrium between a ketone (keto) and aldehyde (enol).