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The reaction often favors formation of the α-glycosidic bond as shown due to the anomeric effect. A glycosidic bond is formed between the hemiacetal or hemiketal group of a saccharide (or a molecule derived from a saccharide) and the hydroxyl group of some compound such as an alcohol. A substance containing a glycosidic bond is a glycoside.
In organic chemistry, glycoside hydrolases can be used as synthetic catalysts to form glycosidic bonds through either reverse hydrolysis (kinetic approach) where the equilibrium position is reversed; or by transglycosylation (kinetic approach) whereby retaining glycoside hydrolases can catalyze the transfer of a glycosyl moiety from an ...
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.
Upon activation of the glycosyl donor group (Y) (usually SR, OAc, or Br group) in the next step, the tethered aglycon traps the developing oxocarbenium ion at C-1, and is transferred from the same face as OH-2, forming the glycosidic bond stereospecifically. The yield of this reaction drops as the bulkiness of the alcohol increases.
Mutation of the active site nucleophile to a non-nucleophilic amino acid prevents the formation of a covalent intermediate. An activated glycosyl donor with a good anomeric-leaving group (often a fluorine) is required. The leaving group is displaced by an alcohol of the acceptor sugar aided by the active site general base amino acid of the enzyme.
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 anomeric carbon of the new glycosidic bond.
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. [1] The resulting reaction is referred to as a glycosylation or chemical ...
The Crich β-mannosylation in organic chemistry is a synthetic strategy which is used in carbohydrate synthesis to generate a 1,2-cis-glycosidic bond.This type of linkate is generally very difficult to make, and specific methods like the Crich β-mannosylation are used to overcome these issues.