A glycosyl acceptor is any suitable
nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they ar ...
-containing molecule that will react with a
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 ...
to form a new
glycosidic bond
A glycosidic bond or glycosidic linkage is a type of covalent bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate.
A glycosidic bond is formed between the hemiacetal or hemiketal group ...
. By convention, the acceptor is the member of this pair which did not contain the resulting
anomer
In carbohydrate chemistry, a pair of anomers () is a pair of near-identical stereoisomers that differ at only the anomeric carbon, the carbon that bears the aldehyde or ketone functional group in the sugar's open-chain form. However, in order f ...
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.
Background
Examples
glucose to haemoglobin
See also
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Chemical glycosylation
A chemical glycosylation reaction involves the coupling of a glycosyl donor, to a glycosyl acceptor forming a glycoside. If both the donor and acceptor are sugars, then the product is an oligosaccharide. The reaction requires activation with a ...
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Glycosyl halide
A glycosyl group is a univalent free radical or substituent structure obtained by removing the hemiacetal hydroxyl group from the cyclic form of a monosaccharide and, by extension, of a lower oligosaccharide.
Glycosyl also reacts with inorganic a ...
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Armed and disarmed saccharides The 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 reac ...
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Carbohydrate chemistry
Carbohydrate chemistry is a subdiscipline of chemistry primarily concerned with the detection, synthesis, structure, and function of carbohydrates. Due to the general structure of carbohydrates, their synthesis is often preoccupied with the sele ...
References
*{{cite journal , last=Van Der Vorm , first=S. , last2=Hansen , first2=T. , last3=Van Hengst , first3=J.M. , last4=Overkleeft , first4=H.S. , last5=Van Der Marel , first5=G.A. , last6=Codée , first6=J.D. , title=Acceptor reactivity in glycosylation reactions , journal=Chemical Society Reviews , volume=48 , issue=17 , pages=4688–4706 , date=2019 , doi=10.1039/C8CS00369F , url=https://pubs.rsc.org/en/content/articlehtml/2019/cs/c8cs00369f , pmid=31287452
Carbohydrate chemistry
Organic reactions