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A glycosidic bond or glycosidic linkage is a type of ether bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate. Formation of ethyl glucoside: Glucose and ethanol combine to form ethyl glucoside and water .
Depending on whether the glycosidic bond lies "below" or "above" the plane of the cyclic sugar molecule, glycosides are classified as α-glycosides or β-glycosides. Some enzymes such as α-amylase can only hydrolyze α-linkages; others, such as emulsin, can only affect β-linkages. There are four type of linkages present between glycone and ...
The formation of a glycosidic linkage results in the formation of a new stereogenic centre and therefore a mixture of products may be expected to result. The linkage formed may either be axial or equatorial (α or β with respect to glucose). To better understand this, the mechanism of a glycosylation reaction must be considered.
The other challenge of chemical glycosylation is the stereoselectivity that each glycosidic linkage has two stereo-outcomes, α/β or cis/trans. Generally, the α- or cis-glycoside is more challenging to synthesis. [19]
O-linked glycosylation is the attachment of a sugar molecule to the oxygen atom of serine (Ser) or threonine (Thr) residues in a protein. O-glycosylation is a post-translational modification that occurs after the protein has been synthesised.
Amylopectin is synthesized by the linkage of α(1→4) Glycosidic bonds. The extensive branching of amylopectin (α(1→6) Glycosidic bond) is initiated by BE and this is what differentiates amylose from amylopectin. DBE is also needed during this synthesis process to regulate the distribution of these branches. [19] [22]
This β-linkage is similar to glycosidic bond between the sugar moieties in the glycan structure as described above. Instead of being attached to a sugar hydroxyl group, the anomeric carbon atom is attached to an amide nitrogen. The energy required for this linkage comes from the hydrolysis of a pyrophosphate molecule. [4]
This can result in different regioselectivity depending on the acceptor resulting in products with different glycosidic linkages. One example is the Agrobacterium sp. β-glucosynthase, which forms a β-1,4-glycoside with glucose as the acceptor, but forms a β-1,3-glycoside with xylose as the acceptor.