Heparan Sulfate [9050-30-0]

Heparan sulfate, a complex and linear polysaccharide, exists as part of glycoproteins named heparan sulfate proteoglycans, which are expressed abundantly on the cell surface and in the extracellular matrix.

Heparan sulfate is a linear polysaccharide and belongs to the family of glycosaminoglycans. Heparan sulfate is composed of glucuronic acid (GlcA) and iduronic acid (IdoA) residues as well as N-acetyl glucosamines (GlcNAc) with various sulfation modifications, and is typically 50-200 disaccharides in length. Heparan sulfate interacts with numerous proteins, including growth factors, morphogens, and adhesion molecules, and thereby regulates important developmental processes in invertebrates and vertebrates. Heparan sulfate chains regulate developmental signaling by acting as co-factors through a variety of mechanisms that include but are not limited to maintenance of morphogen gradients and co-receptor functions^[1]. Heparan sulfate proteoglycans can act as receptors for proteases and protease inhibitors regulating their spatial distribution and activity. Membrane Heparan sulfate proteoglycans act as coreceptors for various tyrosine kinase-type growth factor receptors, lowering their activation threshold or changing the duration of signaling reactions^[2]. Heparan sulfate influences the binding affinity of intestinal epithelium cells to Wnt, thereby promoting activation of canonical Wnt signaling and facilitating regeneration of small intestinal crypts after epithelial injury^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Digestion of heparan sulfate impairs context discrimination in a fear conditioning paradigm and oscillatory network activity in the low theta band after fear conditioning. Thus, heparan sulfate maintains neuronal excitability and, as a consequence, support synaptic plasticity and learning^[4]. FGF-2/FGFR system is involved in the regulation of astrocytic reactivity and/or proliferation in the brain and its action is potentiated by heparan sulfate^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

593.47 (monomer)

C₁₂H₁₉NO₂₀S₃ (monomer)

9050-30-0

Solid

White to off-white

O=S(OCC1O[C@@H](OC)[C@H](NS(=O)(O)=O)[C@@H](OS(=O)(O)=O)[C@H]1O[C@@H]2OC(C(O)=O)[C@H](O[C@@H]3OC(COS(=O)(O)=O)[C@H](O[C@@H]4OC(C(O)=O)[C@H](OC)[C@H](O)[C@H]4OS(=O)(O)=O)[C@H](O)[C@H]3NS(=O)(O)=O)[C@H](O)[C@H]2O)(O)=O.4

Room temperature in continental US; may vary elsewhere.

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

• [1]. Kraushaar DC, et al. Heparan sulfate: a key regulator of embryonic stem cell fate. Biol Chem. 2013 Jun;394(6):741-51.  [Content Brief]

  [2]. Sarrazin S, et al. Heparan sulfate proteoglycans. Cold Spring Harb Perspect Biol. 2011 Jul 1;3(7). pii: a004952.  [Content Brief]

  [3]. Yamamoto S, et al. Heparan sulfate on intestinal epithelial cells plays a critical role in intestinal crypt homeostasis via Wnt/β-catenin signaling. Am J Physiol Gastrointest Liver Physiol. 2013 Aug 1;305(3):G241-9.  [Content Brief]

  [4]. Minge D, et al. Heparan Sulfates Support Pyramidal Cell Excitability, Synaptic Plasticity, and Context Discrimination. Cereb Cortex. 2017 Feb 1;27(2):903-918.  [Content Brief]

  [5]. Gómez-Pinilla F, et al. Regulation of astrocyte proliferation by FGF-2 and heparan sulfate in vivo. J Neurosci. 1995 Mar;15(3 Pt 1):2021-9.  [Content Brief]