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Glycosidic bonds of the form discussed above are known as O-glycosidic bonds, in reference to the glycosidic oxygen that links the glycoside to the aglycone or reducing end sugar. In analogy, one also considers S-glycosidic bonds (which form thioglycosides ), where the oxygen of the glycosidic bond is replaced with a sulfur atom.
They are normally present as glycans: oligosaccharide chains are linked to lipids or to compatible amino acid side chains in proteins, by N- or O-glycosidic bonds. N -Linked oligosaccharides are always pentasaccharides attached to asparagine via a beta linkage to the amine nitrogen of the side chain. [ 7 ]
O-GlcNAc modifications were only recently discovered, but the number of proteins with known O-GlcNAc modifications is increasing rapidly. [7] It is the first example of glycosylation that does not occur on secretory proteins. O-GlcNAc is added to the protein by O-GlcNAc transferase and is removed by O-GlcNAcase in a continuous cycle.
Glycosides can be linked by an O- (an O-glycoside), N- (a glycosylamine), S-(a thioglycoside), or C- (a C-glycoside) glycosidic bond. According to the IUPAC, the name "C-glycoside" is a misnomer; the preferred term is "C-glycosyl compound". [3] The given definition is the one used by IUPAC, which recommends the Haworth projection to correctly ...
The first representatives of main chain unhydrolysable linear polymers made up of levoglucosan units were synthesized in 1985 by anionic polymerization of 2,3-epoxy derivatives of levoglucosan (1,6;2,3-dianhydro-4-O-alkyl-β-D-mannopyranoses). [3] 2,3-Polymer. A wide range of unique monomers with different radical R can be synthesized. [4]
The two glucose units are in the pyranose form and are joined by an O-glycosidic bond, with the first carbon (C 1) of the first glucose linked to the fourth carbon (C 4) of the second glucose, indicated as (1→4). The link is characterized as α because the glycosidic bond to the anomeric carbon (C 1) is in the opposite plane from the CH
O-GlcNAcylation is the process of adding a single N-acetylglucosamine sugar to the serine or threonine of a protein. [4] Comparable to phosphorylation, addition or removal of N-acetylglucosamine is a means of activating or deactivating enzymes or transcription factors. [4]
Unlike the biochemical processes, synthetic glycochemistry relies heavily on protecting groups [18] (e.g. the 4,6-O-benzylidene) in order to achieve desired regioselectivity. The other challenge of chemical glycosylation is the stereoselectivity that each glycosidic linkage has two stereo-outcomes, α/β or cis/trans.