Glycosidic bond

A covalent bond formed from a sugar’s anomeric carbon to an oxygen, nitrogen, sulfur, or carbon atom in another group. It links sugars into larger molecules and attaches sugars to other compounds.

Anomeric carbon: The carbon derived from a sugar’s carbonyl carbon that becomes a new stereocenter in its cyclic form. This is the sugar atom that participates directly in a glycosidic bond.
Monosaccharide: A single sugar unit that cannot be hydrolyzed into simpler carbohydrates. A monosaccharide supplies the anomeric carbon at one end of a glycosidic linkage.
Maltose: A disaccharide of two glucose units joined by an α(1→4) glycosidic linkage. Its linkage is a familiar example of an α-glycosidic bond between sugars.
O-glycosidic bond: A glycosidic bond in which the sugar’s anomeric carbon is joined through oxygen. This is the most common linkage type between sugars and many other groups.
Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group at an electrophilic atom. Many glycosylation reactions form bonds through substitution at the anomeric center.
Hemiacetal: A functional group containing a carbon bonded to both a hydroxyl group and an ether group. A sugar’s cyclic hemiacetal provides the reactive anomeric center.
Cellobiose: A disaccharide of two glucose units joined by a β(1→4) glycosidic linkage. It shows how changing anomeric configuration changes carbohydrate properties.
N-glycosidic bond: A glycosidic bond in which the sugar’s anomeric carbon is joined through nitrogen. It connects ribose or deoxyribose to nitrogenous bases in nucleosides.
Glycosylation: The formation of a glycosidic bond between a sugar and an acceptor molecule. This reaction creates the bond and determines which group receives the sugar.
Acetal: A functional group whose central carbon is bonded to two ether oxygens. O-glycosidic bond formation converts a hemiacetal center into an acetal.

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