Glycosyl
Molecular substituent derived from cyclic monosaccharides From Wikipedia, the free encyclopedia
In organic chemistry, a glycosyl group is a univalent free radical or substituent structure obtained by removing the hydroxyl (−OH) group from the hemiacetal (−CH(OH)O−) group found in the cyclic form of a monosaccharide and, by extension, of a lower oligosaccharide. Glycosyl groups are exchanged during glycosylation from the glycosyl donor, the electrophile, to the glycosyl acceptor, the nucleophile.[1] The outcome of the glycosylation reaction is largely dependent on the reactivity of each partner.[2] Glycosyl also reacts with inorganic acids, such as phosphoric acid, forming an ester such as glucose 1-phosphate.[3]
Examples
In cellulose, glycosyl groups link together 1,4-β-D-glucosyl units to form chains of (1,4-β-D-glucosyl)n. Other examples include ribityl in 6,7-Dimethyl-8-ribityllumazine, and glycosylamines.
Alternative substituent groups
Instead of the hemiacetal hydroxyl group, a hydrogen atom can be removed to form a substituent, for example the hydrogen from the C3 hydroxyl of a glucose molecule. Then the substituent is called D-glucopyranos-3-O-yl as it appears in the name of the drug Mifamurtide.
Recent detection of Au3+ in vivo used C-glycosyl pyrene. Its fluorescence and permeability through cell membranes helped detect Au3+.[4]
See also
References
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