H8892

Heparin disaccharide I-H sodium salt

Name: Heparin disaccharide I-H sodium salt
Brand: SIGMA

Synonym(s):

α-ΔUA-2S-[1→4]-GlcN-6S

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About This Item

Linear Formula:

C₁₂H₁₇NO₁₆S₂Na₂

CAS Number:

136098-04-9

Molecular Weight:

541.37

NACRES:

NA.25

PubChem Substance ID:

329815254

UNSPSC Code:

12352201

MDL number:

MFCD00466926

InChI key

WHYGSGRAJJCXLY-LXROVJCJSA-K

SMILES string

[Na+].[Na+].[Na+].N[C@H]1C(O)O[C@H](COS([O-])(=O)=O)[C@@H](O[C@@H]2OC(=C[C@H](O)[C@H]2OS([O-])(=O)=O)C([O-])=O)[C@@H]1O

InChI

1S/C12H19NO16S2.3Na/c13-6-7(15)9(5(26-11(6)18)2-25-30(19,20)21)28-12-8(29-31(22,23)24)3(14)1-4(27-12)10(16)17;;;/h1,3,5-9,11-12,14-15,18H,2,13H2,(H,16,17)(H,19,20,21)(H,22,23,24);;;/q;3*+1/p-3/t3-,5+,6+,7+,8+,9+,11?,12-;;;/m0.../s1

assay

~99% (HPLC)

form

solid

technique(s)

HPLC: suitable

color

white to faint yellow

storage temp.

−20°C

Application

Heparin disaccharide I-H sodium salt has been used as a non-naphthalene, negatively charged, bivalent compound to test its ability to induce liquid-liquid phase separation (LLPS).

Biochem/physiol Actions

Heparin disaccharide is a bivalent compound with less hydrophobic nature. It elevates the cytosolic calcium (Ca²⁺) extrusion rate and may serve as a potential drug for the activation of Na+ /Ca²⁺ exchanger (NCX).

Products of the digestion of heparin and heparan sulfate by various heparinases

Other Notes

In the following listings, ΔUA = 4-deoxy-L-threo-hex-4-enopyranosyluronic acid; GlcN = D-glucosamine; Ac = Acetyl; NS, 2S, 6S, = N-sulfo, 2-sulfate and 6-sulfate respectively.

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Heparin and heparan sulfate disaccharides bind to the exchanger inhibitor peptide region of Na+/Ca2+ exchanger and reduce the cytosolic calcium of smooth muscle cell lines. Requirement of C4-C5 unsaturation and 1--> 4 glycosidic linkage for activity.

Samuel K Shinjo et al.

The Journal of biological chemistry, 277(50), 48227-48233 (2002-10-11)

Heparin and heparan sulfate fragments, obtained by bacterial heparinase and heparitinases, bearing an unsaturation at C4-C5 of the uronic acid moiety, are able to produce up to 80% reduction of the cytosolic calcium of smooth muscle cell lines. Unsaturated disaccharides

Small molecules as potent biphasic modulators of protein liquid-liquid phase separation.

W Michael Babinchak et al.

Nature communications, 11(1), 5574-5574 (2020-11-06)

Liquid-liquid phase separation (LLPS) of proteins that leads to formation of membrane-less organelles is critical to many biochemical processes in the cell. However, dysregulated LLPS can also facilitate aberrant phase transitions and lead to protein aggregation and disease. Accordingly, there