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l-Iduronic acid (IUPAC abbr.: 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 pyranose sugar. Most pyranoses are stable in one of two chair conformations 1 C 4 ...
For example, D-mannuronic (C-2), D-alluronic (C-3), D-galacturonic (C-4), and L-iduronic acid (C-5) are epimers of glucuronic acid. The nonplanar pyranose rings can assume either chair (in 2 variants) or boat conformation. The preferred conformation depends on spatial interference or other interactions of the substituents. The pyranose form of ...
Glucose (before oxidization) The Fischer projections of D-glucose (left) and D-glucuronic acid (right). Glucose's terminal carbon's primary alcohol group has been oxidized to a carboxylic acid. Uronic acids (/ ʊ ˈ r ɒ n ɪ k /) or alduronic acids are a class of sugar acids with both carbonyl and carboxylic acid functional groups. [1]
Distinguished from chondroitin sulfate by the presence of iduronic acid, although some hexuronic acid monosaccharides may be glucuronic acid. [16] Keratan sulfate: Gal or Gal(6S) GlcNAc or GlcNAc(6S)-Gal(6S)β1-4GlcNAc(6S)β1-3: Keratan sulfate type II may be fucosylated. [21] Heparin: GlcUA or IdoUA(2S) GlcNAc or GlcNS or GlcNAc(6S) or GlcNS(6S)
There is no internationally accepted molecular standard for the composition of heparin, as it is a complex polymer of GAG units and uronic acids (including D-glucuronic acid, L-iduronic acid, and D-glucosamine). Position of N-acetyl, N-sulfate, and O-sulfate groups in these uronic acids can vary, as can the branching patterns of the chain.
The most common disaccharide unit within heparan sulfate is composed of a glucuronic acid (GlcA) linked to N-acetylglucosamine (GlcNAc), typically making up around 50% of the total disaccharide units. Compare this to heparin, where IdoA(2S)-GlcNS(6S) makes up 85% of heparins from beef lung and about 75% of those from porcine intestinal mucosa.
Other oxidized forms of d-galactose are d-galactonic acid (carboxylic group at C1) and meso-galactaric acid (carboxylic groups at C1 and C6). It is also a uronic acid or hexuronic acid. Naturally occurring uronic acids are d-glucuronic acid, d-galacturonic acid, l-iduronic acid and d-mannuronic acid.
It is also known as ascorbic acid water (Vitamin C dissolved in water) The molecular formula C 6 H 10 O 7 (molar mass: 194.14 g/mol, exact mass: 194.0427 u) may refer to: D-Galacturonic acid; Mannuronic acid; Glucuronic acid; Iduronic acid (IdoA)