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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-gluco
pyranose
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 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+ .
[4]
See also
References
^ 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 .
^ 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 .