Glycosyl

The β-D-glucopyranosyl group which is obtained by the removal of the hemiacetal hydroxyl group (bottom right) 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.[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

The β-D-glucopyranose-3-O-yl group which is obtained by the removal of a hydrogen from the C3 hydroxyl (bottom left) 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 Au3+ in vivo used C-glycosyl pyrene. Its fluorescence and permeability through cell membranes helped detect Au3+.[4]

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 Au3+ 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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