Iduronic acid
L-Iduronic acid
Identifiers
CAS number 3402-98-0
PubChem 11877134
ChemSpider 10051462 YesY
KEGG C06472 YesY
MeSH Iduronic+acid
ChEBI CHEBI:28481 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H10O7
Molar mass 194.14 g mol−1
 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

L-Iduronic acid (IdoA) is the major uronic acid component of the glycosaminoglycans (GAGs) dermatan sulfate, and heparin. It is also present in heparan sulfate although here in a minor amount relative to its carbon-5 epimer glucuronic acid.

IdoA is a hexapyranose sugar. Most hexapyranoses are stable in one of two chair conformations 1C4 or 4C1. L-iduronate is different and adopts more than one solution conformation, with an equilibrium existing between three low-energy conformers. These are the 1C4 and 4C1 chair forms and an additional 2S0 skew-boat conformation.

IdoA may be modified by the addition of an O-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 in respiratory syncytial virus 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, the 1C4 and 2S0 conformations (shown below for IdoA2S) predominate.

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

References

  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. http://www.ncbi.nlm.nih.gov/pubmed/10860881. 
  2. ^ Ferro, D. R. Provasoli, A. (1990). "Conformer populations of L-iduronic acid residues in glycosaminoglycan sequences". Carbohydr. Res. 195 (2): 157–167. doi:10.1016/0008-6215(90)84164-P. PMID 2331699. 

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Look at other dictionaries:

  • iduronic acid — The uronic acid of idose; a constituent of dermatan sulfate. * * * idu·ron·ic ac·id (i″du ronґik) the uronic acid derived from idose; L iduronic acid is an epimer of glucuronic acid and a constituent of dermatan sulfate, heparan sulfate,… …   Medical dictionary

  • iduronic acid — (= a L iduronic acid) A uronic acid, derived from the sugar idose, and bearing one terminal carboxyl group. With N acetyl galactosamine 4 sulphate, a component of dermatan sulphate. See iduronidase …   Dictionary of molecular biology

  • iduronic acid — noun A uronic acid that is a component of the glycosaminoglycan heparin …   Wiktionary

  • Glucuronic acid — IUPAC name (2S,3S,4S,5R,6R) 3,4,5,6 Tetrahydroxyoxane 2 carboxylic acid …   Wikipedia

  • Uronic acid — A uronic acid is a sugar acid with both a carbonyl and a carboxylic acid function. It is best thought of as a sugar in which the terminal carbon s hydroxyl function has been oxidized to a carboxylic acid. (Oxidation of the terminal aldehyde… …   Wikipedia

  • D-Galacturonic acid — IUPAC name (2S,3R,4S,5R) 2,3,4,5 Tetrahydroxy 6 oxo hexanoic acid …   Wikipedia

  • IdUA — iduronic acid …   Medical dictionary

  • IdUA — • iduronic acid …   Dictionary of medical acronyms & abbreviations

  • Heparin — Systematic (IUPAC) name see Hep …   Wikipedia

  • Glycosaminoglycan — For other uses of GAGs see Gag (disambiguation) Chondroitin sulfate …   Wikipedia

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