Chemistry:Glycosyl

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Short description: Molecular substituent derived from cyclic monosaccharides
The β-D-glucopyranosyl group which is obtained by the removal of the hemiacetal hydroxyl group from β-D-glucopyranose

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 also reacts with inorganic acids, such as phosphoric acid, forming an ester such as glucose 1-phosphate.[1]

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

The β-D-glucopyranose-3-O-yl group which is obtained by the removal of a hydrogen from the C3 hydroxyl of β-D-glucopyranose

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 the Au3+ in living organism was possible through the use of C-glycosyl pyrene, where its permeability through cell membrane and fluorescence properties were used to detect Au3+.

[2]

See also

References

  1. Davies, Gideon; Henrissat, Bernard (September 1995). "Structures and mechanisms of glycosyl hydrolases". Structure 3 (9): 853–859. doi:10.1016/S0969-2126(01)00220-9. PMID 8535779. 
  2. Dolai, Bholanath; Nayim, Sk; Hossain, Maidul; Pahari, Pallab; Kumar Atta, Ananta (2019-01-15). "A triazole linked C-glycosyl pyrene fluorescent sensor for selective detection of Au3+ in aqueous solution and its application in bioimaging" (in en). Sensors and Actuators B: Chemical 279: 476–482. doi:10.1016/j.snb.2018.09.105. ISSN 0925-4005.