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Glycosyl

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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 groups are exchanged during glycosylation from the glycosyl donor, the electrophile, to the glycosyl acceptor, the nucleophile. The outcome of the glycosylation reaction is largely dependent on the reactivity of each partner. Glycosyl also reacts with inorganic acids, such as phosphoric acid, forming an ester such as glucose 1-phosphate.

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 Au 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 Au.

See also

References

  1. Crich, David (2010-08-17). "Mechanism of a Chemical Glycosylation Reaction". Accounts of Chemical Research. 43 (8): 1144–1153. doi:10.1021/ar100035r. ISSN 0001-4842. PMID 20496888.
  2. van der Vorm, Stefan; van Hengst, Jacob M. A.; Bakker, Marloes; Overkleeft, Herman S.; van der Marel, Gijsbert A.; Codée, Jeroen D. C. (2018-07-02). "Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity". Angewandte Chemie International Edition. 57 (27): 8240–8244. doi:10.1002/anie.201802899. ISSN 1433-7851. PMC 6032835. PMID 29603532.
  3. 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.
  4. 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 Au in aqueous solution and its application in bioimaging". Sensors and Actuators B: Chemical. 279: 476–482. doi:10.1016/j.snb.2018.09.105. ISSN 0925-4005. S2CID 104657218.
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