Guluronic acid

Guluronic acid

α-l-gulopyranuronic acid
Names
IUPAC name
α-l-gulopyranuronic acid
Other names
Gulopyranuronic acid, GulA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • open form: 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-/m1/s1
    Key: IAJILQKETJEXLJ-SQOUGZDYSA-N
  • open form: C(=O)[C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O
Properties
C6H10O7
Molar mass 194.139 g·mol−1
Related compounds
Related uronic acids
 Alluronic acid, Altruronic acid, Arabinuronic acid, Fructuronic acid, Galacturonic acid, Glucuronic acid, Iduronic acid, Lyxuronic acid, Mannuronic acid, Psicuronic acid, Riburonic acid, Ribuluronic acid, Sorburonic acid, Tagaturonic acid, Taluronic acid, Xyluluronic acid, Xyluronic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Guluronic acid is a uronic acid monosaccharide that may be derived from gulose.[1] l-Guluronic acid is a C-3 epimer of l-galacturonic acid and a C-5 epimer of d-mannuronic acid.[2] Along with d-mannuronic acid, l-guluronic acid is a component of alginic acid, a polysaccharide found in brown algae.[3] α-L-Guluronic acid has been found to bind divalent metal ions (such as calcium and strontium) through the carboxylate moiety and through the axial-equatorial-axial arrangement of hydroxyl groups found around the ring.[4]

  1. ^ Oxford Dictionary of Biochemistry and Molecular Biology. Oxford University Press. 2006. ISBN 9780198529170. Retrieved 30 May 2021.
  2. ^ Zhu, Benwei; Yin, Heng (2015). "Alginate lyase: Review of major sources and classification, properties, structure-function analysis and applications". Bioengineered. 6 (3): 125–131. doi:10.1080/21655979.2015.1030543. PMC 4601208. PMID 25831216.
  3. ^ Gacesa, Peter (1992). "Enzymic degradation of alginates". International Journal of Biochemistry. 24 (4): 545–552. doi:10.1016/0020-711x(92)90325-u. PMID 1516726.
  4. ^ Rowbotham, Jack S.; Christopher Greenwell, H.; Dyer, Philip W. (2021). "Opening the Egg Box : NMR spectroscopic analysis of the interactions between s-block cations and kelp monosaccharides". Dalton Transactions. 50 (38): 13246–13255. doi:10.1039/D0DT04375C. ISSN 1477-9226. PMID 34617523.