Glycosyl acceptor
Encyclopedia
A glycosyl acceptor is any suitable nucleophile
-containing molecule that will react with a glycosyl donor
to form a new glycosidic bond
. By convention, the acceptor is the member of this pair which did not contain the resulting anomer
ic carbon of the new glycosidic bond. Since the nucleophilic atom of the acceptor is typically an oxygen atom, this can be remembered using the mnemonic of the acceptor is the alcohol. A glycosyl acceptor can be a mono- or oligosaccharide that contains an available nucleophile, such as an unprotected hydroxyl.
Nucleophile
A nucleophile is a species that donates an electron-pair to an electrophile to form a chemical bond in a reaction. All molecules or ions with a free pair of electrons can act as nucleophiles. Because nucleophiles donate electrons, they are by definition Lewis bases.Nucleophilic describes the...
-containing molecule that will react with a glycosyl donor
Glycosyl donor
A glycosyl donor is a carbohydrate mono- or oligosaccharide that will react with a suitable glycosyl acceptor to form a new glycosidic bond. By convention, the donor is the member of this pair that contains the resulting anomeric carbon of the new glycosidic bond...
to form a new glycosidic bond
Glycosidic bond
In chemistry, a glycosidic bond is a type of covalent bond that joins a carbohydrate molecule to another group, which may or may not be another carbohydrate....
. By convention, the acceptor is the member of this pair which did not contain the resulting anomer
Anomer
In carbohydrate chemistry, an anomer is a special type of epimer. It is one of two stereoisomers of a cyclic saccharide that differs only in its configuration at the hemiacetal or hemiketal carbon, also called the anomeric carbon. Anomerization is the process of conversion of one anomer to the other...
ic carbon of the new glycosidic bond. Since the nucleophilic atom of the acceptor is typically an oxygen atom, this can be remembered using the mnemonic of the acceptor is the alcohol. A glycosyl acceptor can be a mono- or oligosaccharide that contains an available nucleophile, such as an unprotected hydroxyl.
See also
- Chemical glycosylationChemical glycosylationA chemical glycosylation reaction involves the coupling of a sugar to a glycosyl acceptor forming a glycoside. If the acceptor is another sugar, the product is an oligosaccharide. The reaction involves coupling a glycosyl donor to a glycosyl acceptor via activation utilizing a suitable activator...
- Glycosyl halide
- Armed and disarmed saccharidesArmed and disarmed saccharidesThe armed/disarmed approach to glycosylation is an effective way to prevent sugar molecules from self-glycosylation when synthesizing disaccharides. This approach was first recognized when acetylated sugars only acted as glycosyl acceptors when reacted with benzylated sugars...
- Carbohydrate chemistryCarbohydrate chemistryCarbohydrate chemistry is a subdiscipline of chemistry primarily concerned with the synthesis, structure, and function of carbohydrate structures. Due to the general structure of carbohydrates, their synthesis is often preoccupied with the selective formation of glycosidic linkages and the...