Dermatan sulfate

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Dermatan sulfate
Dermatan sulfate.PNG
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Chemical and physical data
Formula C14H21NO15S
Molar mass 475.37 g·mol−1
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Dermatan sulfate is a glycosaminoglycan (formerly called a mucopolysaccharide) found mostly in skin, but also in blood vessels, heart valves, tendons, and lungs.

Contents

It is also referred to as chondroitin sulfate B, [1] although it is no longer classified as a form of chondroitin sulfate by most sources. The formula is C14H21NO15S. This carbohydrate is composed of linear polymers of disaccharide units that contain, N-acetyl galactosamine (GalNAc) and iduronic acid (IdoA). These repeating units are sulfated at a variety of positions. [2] Dermatan sulfate is a component of the compound sulodexide. [3]

Function

Dermatan sulfate may have roles in coagulation, cardiovascular disease, carcinogenesis, infection, wound repair, maintaining the shape of galactosamine 4-sulfate, skin, and fibrosis. [1]

Pathology

Dermatan sulfate accumulates abnormally in several of the mucopolysaccharidosis disorders.

An excess of dermatan sulfate in the mitral valve is characteristic of myxomatous degeneration of the leaflets leading to redundancy of valve tissue and ultimately, mitral valve prolapse (into the left atrium) and insufficiency. This chronic prolapse occurs mainly in women over the age of 60, and can predispose the patient to mitral annular calcification. Mitral valve insufficiency can lead to eccentric (volume dependent or dilated) hypertrophy and eventually left heart failure if untreated.

See also

Related Research Articles

<span class="mw-page-title-main">Mitral valve</span> Valve in the heart connecting the left atrium and left ventricle

The mitral valve, also known as the bicuspid valve or left atrioventricular valve, is one of the four heart valves. It has two cusps or flaps and lies between the left atrium and the left ventricle of the heart. The heart valves are all one-way valves allowing blood flow in just one direction. The mitral valve and the tricuspid valve are known as the atrioventricular valves because they lie between the atria and the ventricles.

<span class="mw-page-title-main">Heparin</span> Anticoagulant

Heparin, also known as unfractionated heparin (UFH), is a medication and naturally occurring glycosaminoglycan. Since heparins depend on the activity of antithrombin, they are considered anticoagulants. Specifically it is also used in the treatment of heart attacks and unstable angina. It is given intravenously or by injection under the skin. Other uses for its anticoagulant properties include inside blood specimen test tubes and kidney dialysis machines.

<span class="mw-page-title-main">Chondroitin sulfate</span> Sulfated glycosaminoglycan (GAG) compound

Chondroitin sulfate is a sulfated glycosaminoglycan (GAG) composed of a chain of alternating sugars. It is usually found attached to proteins as part of a proteoglycan. A chondroitin chain can have over 100 individual sugars, each of which can be sulfated in variable positions and quantities. Chondroitin sulfate is an important structural component of cartilage, and provides much of its resistance to compression. Along with glucosamine, chondroitin sulfate has become a widely used dietary supplement for treatment of osteoarthritis, although large clinical trials failed to demonstrate any symptomatic benefit of chondroitin.

<span class="mw-page-title-main">Mitral valve prolapse</span> Medical condition

Mitral valve prolapse (MVP) is a valvular heart disease characterized by the displacement of an abnormally thickened mitral valve leaflet into the left atrium during systole. It is the primary form of myxomatous degeneration of the valve. There are various types of MVP, broadly classified as classic and nonclassic. In severe cases of classic MVP, complications include mitral regurgitation, infective endocarditis, congestive heart failure, and, in rare circumstances, cardiac arrest.

<span class="mw-page-title-main">Mitral regurgitation</span> Form of valvular heart disease

Mitral regurgitation(MR), also known as mitral insufficiency or mitral incompetence, is a form of valvular heart disease in which the mitral valve is insufficient and does not close properly when the heart pumps out blood. It is the abnormal leaking of blood backwards – regurgitation from the left ventricle, through the mitral valve, into the left atrium, when the left ventricle contracts. Mitral regurgitation is the most common form of valvular heart disease.

<span class="mw-page-title-main">Proteoglycan</span> Class of compounds

Proteoglycans are proteins that are heavily glycosylated. The basic proteoglycan unit consists of a "core protein" with one or more covalently attached glycosaminoglycan (GAG) chain(s). The point of attachment is a serine (Ser) residue to which the glycosaminoglycan is joined through a tetrasaccharide bridge. The Ser residue is generally in the sequence -Ser-Gly-X-Gly-, although not every protein with this sequence has an attached glycosaminoglycan. The chains are long, linear carbohydrate polymers that are negatively charged under physiological conditions due to the occurrence of sulfate and uronic acid groups. Proteoglycans occur in connective tissue.

<span class="mw-page-title-main">Glycosaminoglycan</span> Polysaccharides found in animal tissue

Glycosaminoglycans (GAGs) or mucopolysaccharides are long, linear polysaccharides consisting of repeating disaccharide units. The repeating two-sugar unit consists of a uronic sugar and an amino sugar, except in the case of the sulfated glycosaminoglycan keratan, where, in place of the uronic sugar there is a galactose unit. GAGs are found in vertebrates, invertebrates and bacteria. Because GAGs are highly polar molecules and attract water; the body uses them as lubricants or shock absorbers.

<span class="mw-page-title-main">Valvular heart disease</span> Disease in the valves of the heart

Valvular heart disease is any cardiovascular disease process involving one or more of the four valves of the heart. These conditions occur largely as a consequence of aging, but may also be the result of congenital (inborn) abnormalities or specific disease or physiologic processes including rheumatic heart disease and pregnancy.

<span class="mw-page-title-main">Versican</span> Protein-coding gene in the species Homo sapiens

Versican is a large extracellular matrix proteoglycan that is present in a variety of human tissues. It is encoded by the VCAN gene.

Heparinoids are glycosaminoglycans which are chemically and pharmacologically related to heparin. They include oligosaccharides and sulfated polysaccharides of plant, animal, or synthetic origin. Multiple scientific studies have been conducted on heparinoids.

Iduronidase, sold as Aldurazyme, is an enzyme with the systematic name glycosaminoglycan α-L-iduronohydrolase. It catalyses the hydrolysis of unsulfated α-L-iduronosidic linkages in dermatan sulfate.

<span class="mw-page-title-main">Sulfatase</span> Class of enzymes

Sulfatases EC 3.1.6.- are enzymes of the esterase class that catalyze the hydrolysis of sulfate esters. These may be found on a range of substrates, including steroids, carbohydrates and proteins. Sulfate esters may be formed from various alcohols and amines. In the latter case the resultant N-sulfates can also be termed sulfamates.

Regurgitation is blood flow in the opposite direction from normal, as the backward flowing of blood into the heart or between heart chambers. It is the circulatory equivalent of backflow in engineered systems. It is sometimes called reflux.

<span class="mw-page-title-main">Arylsulfatase B</span> Mammalian protein found in Homo sapiens

Arylsulfatase B is an enzyme associated with mucopolysaccharidosis VI.

<span class="mw-page-title-main">Maroteaux–Lamy syndrome</span> Lysosomal storage disease

Maroteaux–Lamy syndrome, or Mucopolysaccharidosis Type VI (MPS-VI), is an inherited disease caused by a deficiency in the enzyme arylsulfatase B (ARSB). ASRB is responsible for the breakdown of large sugar molecules called glycosaminoglycans. In particular, ARSB breaks down dermatan sulfate and chondroitin sulfate. Because people with MPS-VI lack the ability to break down these GAGs, these chemicals build up in the lysosomes of cells. MPS-VI is therefore a type of lysosomal storage disease.

Sulodexide, traded as Aterina, is a highly purified mixture of glycosaminoglycans composed of heparan sulfate (80%) and dermatan sulfate (20%).

<span class="mw-page-title-main">CHST14</span> Protein-coding gene in the species Homo sapiens

Carbohydrate sulfotransferase 14 is an enzyme that in humans is encoded by the CHST14 gene.

N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase is an enzyme with systematic name 3'-phosphoadenylyl-sulfate:(dermatan)-4-O-sulfo-N-acetyl-D-galactosamine 6-O-sulfotransferase. This enzyme catalyses the following chemical reaction

Dermatan 4-sulfotransferase is an enzyme with systematic name 3'-phospho-5'-adenylyl sulfate:(dermatan)-N-acetyl-D-galactosamine 4-sulfotransferase. This enzyme catalyses the following chemical reaction

Unsaturated chondroitin disaccharide hydrolase (EC 3.2.1.180, UGL, unsaturated glucuronyl hydrolase) is an enzyme with systematic name beta-D-4-deoxy-Delta4-GlcAp-(1->3)-beta-D-GalNAc6S hydrolase. This enzyme catalyses the following chemical reaction

References

  1. 1 2 Trowbridge JM, Gallo RL (September 2002). "Dermatan sulfate: new functions from an old glycosaminoglycan". Glycobiology. 12 (9): 117R–25R. doi: 10.1093/glycob/cwf066 . PMID   12213784.
  2. "Dermatan sulfate".
  3. Lasierra-Cirujeda, J; Coronel, P; Aza, MJ; Gimeno, M (2010). "Use of sulodexide in patients with peripheral vascular disease". Journal of Blood Medicine. 1: 105–115. doi: 10.2147/JBM.S10558 . PMC   3262318 . PMID   22282689. Sulodexide is a highly purified glycosaminoglycan (GAG) obtained from porcine digestive mucosa and is composed of a mixture of 80% heparan sulfate (an electrophoretically fast moving fraction with a low molecular weight of 7000 Da and affinity for antithrombin III) and 20% dermatan sulfate with a high molecular weight (25,000 Da) and affinity for the heparin II cofactor.