Glycosyl

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]

^ 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.
^ 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.
^ 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.