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Glycosyl information


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.[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]

  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.

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Glycosyl

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In organic chemistry, a glycosyl group is a univalent free radical or substituent structure obtained by removing the hydroxyl (−OH) group from the hemiacetal...

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Glycosyl donor

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A glycosyl donor is a carbohydrate mono- or oligosaccharide that will react with a suitable glycosyl acceptor to form a new glycosidic bond. By convention...

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Glycosyltransferase

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from an activated nucleotide sugar (also known as the "glycosyl donor") to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen-...

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Glycoside hydrolase

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In biochemistry, glycoside hydrolases (also called glycosidases or glycosyl hydrolases) are a class of enzymes which catalyze the hydrolysis of glycosidic...

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Enzyme catalysis

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Enzyme catalysis is the increase in the rate of a process by a biological molecule, an "enzyme". Most enzymes are proteins, and most such processes are...

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Glycosylphosphatidylinositol

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Glycosylphosphatidylinositol (pronunciation) or glycophosphatidylinositol (GPI) is a phosphoglyceride that can be attached to the C-terminus of a protein...

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Chemical glycosylation

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chemical glycosylation reaction involves the coupling of a glycosyl donor, to a glycosyl acceptor forming a glycoside. If both the donor and acceptor...

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Glycosyl acceptor

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A glycosyl acceptor is any suitable nucleophile-containing molecule that will react with a glycosyl donor to form a new glycosidic bond. By convention...

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Glycoside hydrolase family 1

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machinery and the prediction of a common fold for several families of glycosyl hydrolases". Proceedings of the National Academy of Sciences of the United...

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Glycosylamine

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consisting of a glycosyl group attached to an amino group, -NR2. They are also known as N-glycosides, as they are a type of glycoside. Glycosyl groups can...

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Glycosylceramidase

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glycosylceramidase (EC 3.2.1.62) catalyzes the following chemical reaction: glycosyl-N-acylsphingosine + H2O ⇌ {\displaystyle \rightleftharpoons } N-acylsphingosine...

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Membrane dipeptidase

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aminodipeptidase, dipeptide hydrolase, dipeptidyl hydrolase, nonspecific dipeptidase, glycosyl-phosphatidylinositol-anchored renal dipeptidase, MBD, MDP, leukotriene...

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Transferase

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catalyse the transfer of specific functional groups (e.g. a methyl or glycosyl group) from one molecule (called the donor) to another (called the acceptor)...

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Glycoside hydrolase family 32

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CAZypedia, an online encyclopedia of carbohydrate active enzymes. Family 32 glycosyl hydrolases comprise two distinct domains. The N-terminal domain, which...

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Glycosylase

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Glycosylases (EC 3.2) are enzymes that hydrolyze glycosyl compounds. They are a type of hydrolase (EC 3). In turn, glycosylases are divided into two groups:...

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Fermentation

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Shikimate pathway Transcription & replication Translation Proteolysis Glycosyl- ation Sugar acids Double/multiple sugars & glycans Simple sugars Inositol-P...

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Biofilm prevention

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matrix and eject biofilm cells forcibly. First shown in P. aeruginosa, a glycosyl hydrolase PslG can trigger biofilm disassembly by disrupting exopolysaccharide...

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Carbohydrate synthesis

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processes. The generation of carbohydrate structures involves linking glycosyl groups like monosaccharides or oligosaccharides through glycosidic bonds...

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Trichloroacetonitrile

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Michel, J. (1984). "Glycosylimidate, 12 Direkte Synthese vonO-α- undO-β-Glycosyl-imidaten". Liebigs Annalen der Chemie. 1984 (7): 1343–1357. doi:10.1002/jlac...

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Glycoside

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IUPAC, the name "C-glycoside" is a misnomer; the preferred term is "C-glycosyl compound". The given definition is the one used by IUPAC, which recommends...

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Carbohydrate

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sources. Glycobiology Glycogen Glycoinformatics Glycolipid Glycome Glycomics Glycosyl Macromolecule Saccharic acid Avenas P (2012). "Etymology of main polysaccharide...

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