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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.
This group, under the reaction conditions, is activated and via the formation of an oxocarbenium is eliminated leaving an electrophilic anomeric carbon. A glycosyl acceptor is a sugar with an unprotected nucleophilic hydroxyl group which may attack the carbon of the oxocarbenium ion formed during the reaction and allow for the formation of the ...
A C-C bond is formed between the first carbon of the alpha-mannose and the second carbon of the tryptophan. [13] However, not all the sequences that have this pattern are mannosylated. It has been established that, in fact, only two thirds are and that there is a clear preference for the second amino acid to be one of the polar ones (Ser, Ala ...
Glycosynthase are derived from glycosidase enzymes, which catalyze the hydrolysis of glycosidic bonds. [2] They were traditionally formed from retaining glycosidase by mutating the active site nucleophilic amino acid (usually an aspartate or glutamate ) to a small non-nucleophilic amino acid (usually alanine or glycine ).
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 different types of lipid-linked oligosaccharide (LLO) precursor produced in different organisms.. N-linked glycosylation is the attachment of an oligosaccharide, a carbohydrate consisting of several sugar molecules, sometimes also referred to as glycan, to a nitrogen atom (the amide nitrogen of an asparagine (Asn) residue of a protein), in a process called N-glycosylation, studied in ...
Salicin, a glycoside related to aspirin Chemical structure of oleandrin, a cardiac glycoside. In chemistry, a glycoside / ˈ ɡ l aɪ k ə s aɪ d / is a molecule in which a sugar is bound to another functional group via a glycosidic bond.
Most glycosyltransferase enzymes form one of two folds: GT-A or GT-B. Glycosyltransferases (GTFs, Gtfs) are enzymes that establish natural glycosidic linkages.They catalyze the transfer of saccharide moieties from an activated nucleotide sugar (also known as the "glycosyl donor") to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen- carbon-, nitrogen-, or sulfur ...