guluronic acid Chemical Properties

form 

Solid

color 

White to off-white

InChI

InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3-,4+,5-/m0/s1

InChIKey

IAJILQKETJEXLJ-KLVWXMOXSA-N

SMILES

O=C[C@@H]([C@@H]([C@H]([C@@H](C(O)=O)O)O)O)O

guluronic acid Usage And Synthesis

Description

Glucuronic acid is a sugar acid derived from glucose, with its sixth carbon atom oxidized to a carboxylic acid. In living beings, this primary oxidation occurs with UDP-α-D-glucose (UDPG), not with the free sugar.
Glucuronic acid, like its precursor glucose, can exist as a linear (carboxo-)aldohexose (<1%), or as a cyclic hemiacetal (furanose or pyranose). Aldohexoses such as D-glucose are capable of forming two furanose forms (α and β) and two pyranose forms (α and β). By the Fischer convention, glucuronic acid has two stereoisomers (enantiomers), D- and L-glucuronic acid, depending on its configuration at C-5. Most physiological sugars are of the D-configuration. Due to ring closure, cyclic sugars have another asymmetric carbon atom (C-1), resulting in two more stereoisomers, named anomers. Depending on the configuration at C-1, there are two anomers of glucuronic acid, α- and β-form. In β-D-glucuronic acid the C-1 hydroxy group is on the same side of the pyranose ring as the carboxyl group. In the free sugar acid, the β-form is prevalent (~64%), whereas in the organism, the α-form UDP-α-D-glucuronic acid (UDPGA) predominates.

Uses

Guluronic acid (G2013), one of the organic building blocks of hyaluronic acid, is a nonsteroidal anti-inflammatory agent has favorable anti-inflammatory effect[1][2].

References

[1] Amaniampong PN, et al. Selective and Catalyst-free Oxidation of D-Glucose to D-Glucuronic acid induced by High-Frequency Ultrasound. Sci Rep. 2017;7:40650. Published 2017 Jan 13. DOI:10.1038/srep40650
[2] Nazeri S, et al. The safety and efficacy of Guluronic acid (G2013) in ankylosing spondylitis: A randomized controlled parallel clinical trial. Pharmacol Rep. 2019;71(3):393-398. DOI:10.1016/j.pharep.2019.02.002

guluronic acid(15769-56-9)Related Product Information

• D-mannuronic acid sodium salt
• D-dimannuronic acid disodium salt
• D-tetramannuronic acid tetrasodium salt
• D-octamannuronic acid octasodium salt
• D-hexamannuronic acid hexasodium salt
• D-heptamannuronic acid heptasodium salt
• D-trimannuronic acid trisodium salt
• manninotriose
• D-pentamannuronic acid pentasodium salt
• Perisesaccharide B
• D-Glucuronic acid
• 2-oxogluconic acid
• L-xylo-hex-2-ulosonic acid
• L-hexaguluronic acid hexasodium salt
• L-heptaguluronic acid heptasodium salt
• L-diguluronic acid disodium salt
• L-decaguluronic acid decasodium salt