CHEMISTRY GLOSSARY

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.

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).

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.