Glycosyl
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In
organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
, a glycosyl group is a univalent free radical or
substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...
structure obtained by removing the hydroxyl () group from the hemiacetal () group found in the cyclic form of a
monosaccharide Monosaccharides (from Greek '' monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. Chemically, monosaccharides are polyhy ...
and, by extension, of a lower
oligosaccharide An oligosaccharide (; ) is a carbohydrate, saccharide polymer containing a small number (typically three to ten) of monosaccharides (simple sugars). Oligosaccharides can have many functions including Cell–cell recognition, cell recognition and ce ...
. Glycosyl groups are exchanged during
glycosylation Glycosylation is the reaction in which a carbohydrate (or ' glycan'), i.e. a glycosyl donor, is attached to a hydroxyl or other functional group of another molecule (a glycosyl acceptor) in order to form a glycoconjugate. In biology (but not ...
from the glycosyl donor, the
electrophile In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively Electric charge, charged, have an ...
, to the glycosyl acceptor, the
nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
. The outcome of the glycosylation reaction is largely dependent on the reactivity of each partner. Glycosyl also reacts with inorganic acids, such as
phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, ...
, forming an
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
such as glucose 1-phosphate.


Examples

In
cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...
, 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 6,7-Dimethyl-8-ribityllumazine is a precursor for riboflavin. It is acted upon by riboflavin synthase. Pteridines Imides {{biochem-stub ...
, and glycosylamines.


Alternative substituent groups

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 Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...
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+.


See also

* Acyl group


References

{{Reflist Substituents Biomolecules Monosaccharides Oligosaccharides