CHEMISTRY GLOSSARY

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).

acetal    →   acetal

Acetals are organic compounds having the structure R₂C(OR’)₂ (R’ ≠ H). They are organic compounds formed by addition of alcohol molecules to aldehyde or ketone molecules. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R’ groups. The formation of acetals is reversible; acetals can be hydrolysed back to aldehydes (ketone) in acidic solutions.

Acetal, 1,1-diethoxyethane (CH₃CH(OC₂H₅)₂), is an organic compound, pleasant smelling, formed by addition of ethyl alcohol to ethanal (acetaldehyde). It is used as a solvent and in synthetic organic chemistry.

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.

glycosyl group    →   glikozidna skupina

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

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.

hemiketal    →   poluketal

Hemiketals are organic compounds having the structure R₂C(OH)OR (R ≠ H), derived from ketones by formal addition of an alcohol to the carbonyl group. The rings of ketose sugars are hemiketals. This term, once abandoned, has been reinstated as a subclass of hemiacetals.

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.

ketal    →   ketal

Ketals are organic compounds formed by addition of an alcohol to a ketone. If one molecule of ketone (RR’CO) reacts with one molecule of alcohol (R"OH) then a hemiketal is formed. The rings of ketose sugars are hemiketals. Further reaction produces a full ketal (RR’C(OR")₂). This term, once abandoned, has been reinstated as a subclass of acetals.

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.