Description
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
1C
4 or
4C
1. L-iduronate is different and adopts more than one solution conformation, with an equilibrium existing between three low-energy conformers. These are the
1C
4 and
4C
1 chair forms and an additional
2S
0 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. When internally positioned within an oligosaccharide, the
1C
4 and
2S
0 conformations (shown below for IdoA2S) predominate. Proton NMR spectroscopy can be used to track changes in the balance of this equilibrium.
