1. Solid state structure of sodium β-1-thiophenyl glucuronate identifies 5-coordinate sodium with three independent glucoronates.
- Author
-
Alharthi, Fahad Ayesh, Whitehead, George F.S., Vitórica-Yrezábal, Iñigo J., and Gardiner, John M.
- Subjects
- *
GLYCOSAMINOGLYCANS , *SODIUM , *GLUCURONIC acid , *URONIC acids , *HEPARAN sulfate , *MORPHOLOGY - Abstract
Glucuronic acid is a key component of the glycosaminoglycans (GAGs) Chrondroitin Sulfate (CS), Heparin/Heparan sulfate (HS) and Hyaluronic Acid (HA), as well an important metabolite derivative. In biological systems the carboxylate of uronic acids in GAGs is involved in important H-binding interactions, and the role of metal coordination, such as sodiated systems, has indications associated with a number of biological effects, and physiological GAG-related processes. In synthetic approaches to GAG fragments, thioglycoside intermediates, or derivatives from these, are commonly employed. Of the reported examples of sodium coordination in carbohydrates, 6-coordinate systems are usually observed often with water ligands involved, Herein we report an unexpected 5-coordinate sodiated GlcA crystal structure of the parent GlcA, but as a thioglycoside derivative, whose crystal coordination differs from previous examples, with no involvement of water as a ligand and containing a distorted trigonal bypramidal sodium with each GlcA having five of 6 oxygens sodium-coordinated. [Display omitted] • Unusual 5-coordinate sodiated GlcA thioglucoside crystal structure with all ligands from carbohydrate oxygens. • The GlcA thioglycoside is a new derivative. • Shows 3 sodium environments per sugar, two chelated (one each from the carboxylate) and the third only monocoordinate O3. • New example of geometries that are accessible for the GlcA fragment which may be of relevance in biological GlcA structures. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF