Dermatan sulfate: Difference between revisions

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Updating {{drugbox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia talk:WikiProject
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{{Short description|Glycosaminoglycan found in animals}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
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| verifiedrevid = 426919299
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| verifiedrevid = 447549315
| image = Dermatan sulfate.PNG
| image = Dermatan sulfate.PNG
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<!--Clinical data -->

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| tradename =
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<!--Clinical data-->
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| tradename =
| Drugs.com = {{drugs.com|international|dermatan-sulfate}}
| Drugs.com = {{drugs.com|international|dermatan-sulfate}}
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
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<!--Identifiers -->

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| CAS_number = 24967-94-0
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<!--Chemical data -->

| C=14 | H=21 | N=1 | O=15 | S=1
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<!--Chemical data-->
| molecular_weight =
| smiles = [O-]C(=O)[C@@H]2O[C@@H](O[C@H]1[C@@H](OS([O-])(=O)=O)[C@H](O[C@@H](O)[C@@H]1NC(=O)C)CO)[C@H](O)[C@@H](O)[C@@H]2O
|drug_name=|alt=|caption=|type=|MedlinePlus=|legal_status=|licence_EU=|pregnancy_category=|licence_US=|DrugBank=}}
| InChI = 1/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)/p-2/t4-,5-,6+,7+,8-,9+,10-,11-,13-,14-/m1/s1
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| StdInChIKey = AVJBPWGFOQAPRH-FWMKGIEWSA-L
}}
'''Dermatan sulfate''' is a [[glycosaminoglycan]] (formerly called a mucopolysaccharide) found mostly in [[skin]], but also in [[blood vessels]], [[heart valves]], [[tendons]], and [[lungs]].
'''Dermatan sulfate''' is a [[glycosaminoglycan]] (formerly called a mucopolysaccharide) found mostly in [[skin]], but also in [[blood vessels]], [[heart valves]], [[tendons]], and [[lungs]].


It is also referred to as [[chondroitin sulfate|chondroitin sulfate B]], <ref>{{cite journal | last = Trowbridge | first = JM | coauthors = Gallo, RL | title = Dermatan sulfate: new functions from an old glycosaminoglycan | journal = Glycobiology | volume = 12 | issue = 9 | pages = 117R–25R | year = 2002 | month = September | pmid = 12213784 | doi = 10.1093/glycob/cwf066 }}</ref> although it is no longer classified as a form of chondroitin sulfate by most sources.
It is also referred to as [[chondroitin sulfate|chondroitin sulfate B]],<ref name = "Trowbridge_2002">{{cite journal | vauthors = Trowbridge JM, Gallo RL | title = Dermatan sulfate: new functions from an old glycosaminoglycan | journal = Glycobiology | volume = 12 | issue = 9 | pages = 117R–125R | date = September 2002 | pmid = 12213784 | doi = 10.1093/glycob/cwf066 | doi-access = free }}</ref> although it is no longer classified as a form of chondroitin sulfate by most sources. The formula is C<sub>14</sub>H<sub>21</sub>NO<sub>15</sub>S. 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.<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/Dermatan-sulfate|title = Dermatan sulfate}}</ref> Dermatan sulfate is a component of the compound [[sulodexide]].<ref name="Lasierra-Cirujeda 2010">{{cite journal | vauthors = Lasierra-Cirujeda J, Coronel P, Aza M, Gimeno M | title = Use of sulodexide in patients with peripheral vascular disease | journal = Journal of Blood Medicine | volume = 1 | pages = 105–115 | date = 2010 | pmid = 22282689 | pmc = 3262318 | doi = 10.2147/JBM.S10558 | quote = 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. | doi-access = free }}</ref>


==Function==
== Function ==
Dermatan sulfate may have roles in [[coagulation]], [[cardiovascular disease]], [[carcinogenesis]], [[infection]], [[wound repair]], and [[fibrosis]].{{Citation needed|date=February 2011}}
Dermatan sulfate may have roles in [[coagulation]], [[cardiovascular disease]], [[carcinogenesis]], [[infection]], [[wound repair]], maintaining the shape of galactosamine 4-sulfate, skin, and [[fibrosis]].<ref name = "Trowbridge_2002" />


==Pathology==
==Pathology==
Dermatan sulfate accumulates abnormally in several of the [[mucopolysaccharidosis]] disorders.
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.
An excess of dermatan sulfate in the [[mitral valve]] is characteristic of myxomatous degeneration of the leaflets leading to redundancy of valve [[tissue (biology)|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 insufficiency|Mitral valve insufficiency]] can lead to eccentric (volume dependent or dilated) [[Hypertrophic cardiomyopathy|hypertrophy]] and eventually [[left heart]] failure if untreated.


==See also==
== See also ==
* [[iduronic acid]]
* [[Iduronic acid]]


==External links==
== References ==
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{{reflist}}

== External links ==
* {{MeshName|Dermatan+sulfate}}
* {{MeshName|Dermatan+sulfate}}

==References==
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{{reflist}}


{{Antithrombotics}}
{{Antithrombotics}}
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[[Category:Glycosaminoglycans]]
[[Category:Glycosaminoglycans]]
[[Category:Sulfate esters]]


{{biochem-stub}}

{{pharma-stub}}

[[ca:Sulfat dermatà]]
[[el:Θειική δερματάνη]]
[[fa:درماتان سولفات]]
[[it:Dermatan solfato]]
[[ja:デルマタン硫酸]]
[[pt:Sulfato de dermatan]]
[[fi:Dermataanisulfaatti]]
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