Iduronic acid
| Structural formula | |||||||||||||
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| Structural formula of L- iduronic acid in the Aldo form | |||||||||||||
| General | |||||||||||||
| Surname | Iduronic acid | ||||||||||||
| other names |
IduA |
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| Molecular formula | C 6 H 10 O 7 | ||||||||||||
| External identifiers / databases | |||||||||||||
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| properties | |||||||||||||
| Molar mass | 194.14 g mol −1 | ||||||||||||
| Physical state |
firmly |
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| Melting point |
131-132 ° C |
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| safety instructions | |||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||
Iduronic acid is a chemical compound from the group of uronic acids , more precisely the uronic acid of idose . The anion is called iduronate .
Isomers
There are two stereoisomeric forms of iduronic acid , the naturally occurring L -iduronic acid and the practically meaningless D -iduronic acid.
properties
L -iduronic acid is a component of glycosaminoglycans , for example chondroitin sulfate B and heparin . It is a stereoisomer of glucuronic and produced by epimerization of D -Glucuronsäure at the carboxy group .
Disulfated iduronic acid inhibits the communication between T lymphocytes by competitively inhibiting the binding of heparan sulfate to the chemokine CCL20. This makes the substance interesting for a development for the treatment of the inflammation of the bronchial mucosa associated with asthma .
Web links
- Maurice Petitou, Pierre Sinaÿ et al .: Synthesis of conformationally fixed carbohydrates: A skew- boat conformation of L-iduronic acid in heparin determines its antithrombotic activity . In: Angewandte Chemie . tape 113 , no. 9 , May 4, 2001, p. 1723-1726 , doi : 10.1002 / 1521-3757 (20010504) 113: 9 <1723 :: AID-ANGE17230> 3.0.CO; 2-N ( PDF ).
Individual evidence
- ↑ Entry on L- iduronic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 23, 2014.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ External identifiers or database links for D-iduronic acid : CAS number: 3402-98-0, PubChem : 18845 , ChemSpider : 17794 , Wikidata : Q418846 .
- ↑ Rudolf Hänsel, Otto Sticher: Pharmakognosie - Phytopharmazie . Springer, 2009, ISBN 978-3-642-00962-4 ( page 614 in the Google book search).
- ↑ Sugar against shortness of breath. A simple molecule inhibits the inflammation associated with asthma at an early stage June 11, 2014