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Iduronic acid

From Wikipedia, the free encyclopedia
Iduronic acid
Names
IUPAC name
l-idopyranuronic acid
Other names
l-Iduronic acid,d-ido-Hexuronic acid, IdoA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSHIduronic+acid
UNII
  • InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/p-1/t1-,2-,3+,4+,6+/m0/s1 checkY
    Key: AEMOLEFTQBMNLQ-VCSGLWQLSA-M checkY
  • InChI=1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/p-1/t1-,2-,3+,4+,6+/m0/s1
    Key: AEMOLEFTQBMNLQ-QQSWGHAIBB
  • [O-]C(=O)[C@@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
C6H10O7
Molar mass194.139 g/mol
Appearancewhite solid
Melting point131–132 °C (268–270 °F; 404–405 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

l-Iduronic acid (IUPAC abbr.:IdoA) is the majoruronic acid component of theglycosaminoglycans (GAGs)dermatan sulfate, andheparin. It is also present inheparan sulfate, although here in a minor amount relative to its carbon-5epimerglucuronic acid.

IdoA is apyranose sugar. Most pyranoses are stable in one of two chair conformations1C4 or4C1.l-iduronate is different and adopts more than one solution conformation, with an equilibrium existing between three low-energy conformers. These are the1C4 and4C1 chair forms and an additional2S0 skew-boatconformation.[citation needed]

α-l-idopyranuronic acid

IdoA may be modified by the addition of anO-sulfate group at carbon position 2 to form 2-O-sulfo-l-iduronic acid (IdoA2S).

In 2000, LK Hallak described the importance of this sugar inrespiratory syncytial virus (RSV) infection. Dermatan sulfate and heparan sulfate were the only GAGs containing IdoA, and they were the only ones that inhibited RSV infection in cell culture.[1]

When internally positioned within an oligosaccharide, the1C4 and2S0 conformations (shown below for IdoA2S) predominate.

ProtonNMR spectroscopy can be used to track changes in the balance of this equilibrium.[2]

  • IdoA(2S)1C4 conformation
    IdoA(2S)1C4 conformation
  • IdoA(2S)2S0 conformation
    IdoA(2S)2S0 conformation

Iduronic acid can be detected colorimetrically.[3]

See also

[edit]

References

[edit]
  1. ^Hallak LK, Collins PL, Knudson W, Peeples ME (2000)."Iduronic acid-containing glycosaminoglycans on target cells are required for efficient respiratory syncytial virus infection".Virology.271 (2):264–75.doi:10.1006/viro.2000.0293.PMID 10860881.
  2. ^Ferro DR, Provasoli A, Ragazzi M, Casu B, Torri G, Bossennec V, Perly B, Sinaÿ P, Petitou M, Choay J (1990). "Conformer populations of L-iduronic acid residues in glycosaminoglycan sequences".Carbohydrate Research.195 (2):157–167.doi:10.1016/0008-6215(90)84164-P.PMID 2331699.
  3. ^.doi:10.1021/ac50043a036.{{cite journal}}:Cite journal requires|journal= (help);Missing or empty|title= (help)
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