Classification Term: 3764

Disaccharide sulfates (ontology term: CHEMONTID:0003307)

Disaccharides carrying one or more sulfate group on a sugar unit." []

found 5 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Disaccharides

Child Taxonomies: There is no child term of current ontology term.

Heparan sulfate

(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulphooxy)amino]-2-[(sulphooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulphooxy)oxane-2-carboxylic acid

C14H25NO21S3 (639.00812)


Heparan sulfate (HS) is a linear polysaccharide that belongs to the class of compounds known as glycosaminoglycans (PMID: 24146040). It is found in all animal tissues and consists of repeating subunits of N-acetylglucosamine and glucuronic acid, and closely related in structure to heparin. It occurs as a proteoglycan (HSPG) in which two or three HS chains are attached to either cell surface components or the extracellular matrix (ECM), where they serve to reinforce cell adhesion (PMID: 27241222). HS synthesis starts with the transfer of xylose from UDP-xylose by the enzyme known as xylosyltransferase (XT) to specific serine residues within the protein core. Attachment of two galactose (Gal) residues by galactosyltransferases I and II (GalTI and GalTII) and glucuronic acid (GlcA) by the enzyme glucuronosyltransferase I (GlcATI) completes the formation of a tetrasaccharide linker. After attachment of the first N-acetylglucosamine (GlcNAc) residue by the enzyme known as GalNAc Transferase I (GalNAcT-I), elongation of the tetrasaccharide linker is continued by the stepwise addition of GlcA and GlcNAc residues. These are transferred from their respective UDP-sugar nucleotides. HS functions through binding to a variety of protein ligands including interferon gamma, Wnt, antithrombin III, interleukin 8, fibroblast growth factor, endostatin and others. HS thereby regulates a wide range of developmental signaling pathways such as the Wnt, Hedgehog, transforming growth factor-β, and fibroblast growth factor pathways (PMID: 15563523). Heparan sulfate plays a role in a number of biological activities, including developmental processes, angiogenesis, blood coagulation, abolishing detachment activity by GrB (Granzyme B) and tumour metastasis. A heteropolysaccharide that is similar in structure to heparin. It accumulates in individuals with mucopolysaccharidosis.

   

Heparin

Heparinsodiumsalt

(C12H19NO19S3)nH2O (5769154.4632218005)


Heparin is a highly acidic heterogeneous mucopolysaccharide consisting of a variably sulfated repeating disaccharide unit. The most common repeating unit is a trisulfated disaccharide composed of a 2-O-sulfated iduronic acid and 6-O-sulfated, N-sulfated glucosamine, IdoA(2S)-GlcNS(6S). Heparin is formed from equal parts sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from six to twenty thousand. Heparin occurs in and is obtained from liver, lungs, and mast cells of vertebrates. Its function is unknown, but it is used to prevent blood clotting, in vivo and in vitro, in the form of many different salts. Enoxaparin is a low molecular weight heparin. It is used to prevent and treat deep vein thrombosis or pulmonary embolism, and is given as a subcutaneous injection. Enoxaparin binds to and accelerates the activity of antithrombin III. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of coagulation factors Xa and IIa. Factor Xa catalyzes the conversion of prothrombin to thrombin, so enoxaparins inhibition of this process results in decreased thrombin and ultimately the prevention of fibrin clot formation. Low molecular weight heparins are less effective at inactivating factor IIa due to their shorter length compared to unfractionated heparin. A highly acidic mucopolysaccharide formed of equal parts of sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from six to twenty thousand. Heparin occurs in and is obtained from liver, lung, mast cells, etc., of vertebrates. Its function is unknown, but it is used to prevent blood clotting in vivo and vitro, in the form of many different salts. [HMDB]

   

Sucralfate

[({[(2S,3R,4S,5R,6R)-4,5-bis({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)-6-[({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)methyl]-2-{[(2R,3S,4S,5R)-3,4,5-tris({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)-2-[({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)methyl]oxolan-2-yl]oxy}oxan-3-yl]oxy}sulfonyl)oxy]alumanediol

C11H28Al8O51S8 (1447.5886578)


Sucralfate is only found in individuals that have used or taken this drug. It is a basic aluminum complex of sulfated sucrose. [PubChem]Although sucralfates mechanism is not entirely understood, there are several factors that most likely contribute to its action. Sucralfate, with its strong negative charge, binds to exposed positively-charged proteins at the base of ulcers. In this way, it coats the ulcer and forms a physical barrier that protects the ulcer surface from further injury by acid and pepsin. It directly inhibits pepsin (an enzyme that breaks apart proteins) in the presence of stomach acid and binds bile salts coming from the liver via the bile thus protecting the stomach lining from injury caused by the bile acids. Sucralfate may increase prostaglandin production. Prostaglandins are known to protect the lining of the stomach and may also bind epithelial growth factor and fibroblast growth factor, both of which enhance the growth and repair mechanism of the stomach lining.

   

[(2R,3S,4S,5R)-2,4-Disulfooxy-5-(sulfooxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trisulfooxy-6-(sulfooxymethyl)oxan-2-yl]oxyoxolan-3-yl] hydrogen sulfate

[(2R,3S,4S,5R)-2,4-Disulphooxy-5-(sulphooxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trisulphooxy-6-(sulphooxymethyl)oxan-2-yl]oxyoxolan-3-yl] hydrogen sulphuric acid

C11H20O35S8 (967.755093)


   

Sucrosofate

[4-(Sulphooxy)-2,5-bis[(sulphooxy)methyl]-2-{[3,4,5-tris(sulphooxy)-6-[(sulphooxy)methyl]oxan-2-yl]oxy}oxolan-3-yl]oxidanesulphonic acid

C12H22O35S8 (981.7707422000001)