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Chemia 3

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An oligosaccharide (/ˌɑlɪgoʊˈsækəˌɹaɪd/;[1] from the Greek ὀλίγος olígos, "a few",

and σάκχαρ sácchar, "sugar") is a saccharide polymer containing a small number


(typically three to ten[2][3][4][5]) of monosaccharides (simple sugars).
Oligosaccharides can have many functions including cell recognition and cell
adhesion.[6]

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] Alternately, O-linked
oligosaccharides are generally attached to threonine or serine on the alcohol group
of the side chain. Not all natural oligosaccharides occur as components of
glycoproteins or glycolipids. Some, such as the raffinose series, occur as storage
or transport carbohydrates in plants. Others, such as maltodextrins or
cellodextrins, result from the microbial breakdown of larger polysaccharides such
as starch or cellulose.

Glycosylation
In biology, glycosylation is the process by which a carbohydrate is covalently
attached to an organic molecule, creating structures such as glycoproteins and
glycolipids.[8]

N-Linked glycosylation involves oligosaccharide attachment to asparagine via a beta


linkage to the amine nitrogen of the side chain.[7] The process of N-linked
glycosylation occurs cotranslationally, or concurrently while the proteins is being
translated. Since it is added cotranslationally, it is believed that N-linked
glycosylation helps determine the folding of polypeptides due to the hydrophilic
nature of sugars. All N-linked oligosaccharides are pentasaccharides: five
monosaccharides long.

In N-glycosylation for eukaryotes, the oligosaccharide substrate is assembled right


at the membrane of the endoplasmatic reticulum.[9] For prokaryotes, this process
occurs at the plasma membrane. In both cases, the acceptor substrate is an
asparagine residue. The asparagine residue linked to an N-linked oligosaccharide
usually occurs in the sequence Asn-X-Ser/Thr,[7] where X can be any amino acid
except for proline, although it is rare to see Asp, Glu, Leu, or Trp in this
position.

O-Linked oligosaccharides
Oligosaccharides that participate in O-linked glycosylation are attached to
threonine or serine on the hydroxyl group of the side chain.[7] O-linked
glycosylation occurs in the Golgi apparatus, where monosaccharide units are added
to a complete polypeptide chain. Cell surface proteins and extracellular proteins
are O-glycosylated.[10] Glycosylation sites in O-linked oligosaccharides are
determined by the secondary and tertiary structures of the polypeptide, which
dictate where glycosyltransferases will add sugars.

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