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Natural Polysaccharide and Chemically-modified Polysaccharide Series

Neutral Polysaccharides

Neutral polysaccharides are composed of neutral monosaccharides such as glucose and xylose linked by glycosidic bonds and are polymerized as macromolecules in the range of thousands to millions. They are known to exhibit various properties depending on the type of composed monosaccharides, the bonding position, the presence / absence of side chains / branches, and so on. Since these polysaccharides have many hydroxyl groups (OH), they show affinity for water molecules. they act as hydrophilic colloids holding a large number of water molecules due to their properties. For industrial use, they are widely used for various purposes such as dispersion stabilization, suspension stabilization, viscosity imparting, gel-forming ability, film-forming feature, and adhesive effect.1)

Neutral Polysaccharides

 
Product No.Product NameMain Chain linkages Constituent Monosaccharides
A0456Amylopectinα1-4, [Branches α1-6]Glc
D1449Dextranα1-6Glc
L0088Laminaranβ1-3, [Branches β1-6]Glc
P0978Pullulanα1-4 and α1-6Glc
α1-6 bonds of (Glcα 1-4 Glc α1-4 Glc) unit
X0078Xylanβ1-4, [Side chains α1-2, α1-3]Main chains: Xyl
Side chains: Ara, 4-O-Me-GlcA
C0072Chitinβ1-4GlcNAc

‡Since polysaccharides are heterogeneous compounds, representative main chain linkages and constituent monosaccharides are shown.

 

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Acidic Polysaccharides

Acidic polysaccharides contain a lot of uronic acids (a compound in which the terminal hydroxy group [-CH2OH] of aldohexose is oxidized to a carboxy group [-COOH]) and several sulfate groups (a compound in which the hydroxy group [-OH] of aldohexose is dehydrated condensation with sulfuric acid). These polysaccharides are thought to function with mechanisms that maintain the structure of plant tissues and protect them from exogenous substances. Polyuronic acid-containing pectin and gum arabic are found in land plants while polyuronic acid-containing alginic acid, sulfate group-containing carrageenan and fucoidan are obtained from seaweeds. For practical use, they are widely used for purposes such as imparting viscosity, adhesive effect, dispersion stabilization, aggregation suppression, protein stabilization, and gel-forming ability.2)

Acidic Polysaccharides

 
Product No.Product NameMain Chain linkages Constituent Monosaccharides
A0733Alginic Acidβ1-4ManA, GulA
P0024Pectinα1-4GalA, GalA[COOMe]
X0048Xanthan Gumβ1-4, [Side chains α1-3]Main chains: Glc
Side chains: Man, GlcA
C1804κ-Carrageenanα1-3Gal(4S)β1-4Anhydro-GalGal(4S), 3,6-Anhydro-Gal
C1805ι-Carrageenanα1-3Gal(4S)β1-4Anhydro-Gal(2S)Gal(4S), 3,6-Anhydro-Gal(2S)
C3313λ-Carrageenanα1-3Gal(2S)β1-4Gal(2S, 6S)Gal(2S, 6S), Gal(2S)

‡Since polysaccharides are heterogeneous compounds, representative main chain linkages and Constituent monosaccharides are shown. The sulfate group in paren thesis is the OH position that can be introduced.

 

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Acidic Polysaccharides (Glycosaminoglycans)

Glycosaminoglycans (GAGs) are long linear polysaccharides that form repeating disaccharide structures and have long been studied as systematic names for mucopolysaccharides. It is well known that it functions as a molecule of the extracellular matrix to support tissues present throughout the body. Due to their negative charge and binding to bioactive molecules, GAGs are intimately involved in the regulation of many cellular functions. In vivo, hyaluronic acid (HA) generally exists as a free sugar chain, but chondroitin sulfate (CS), dermatan sulfate (DS), keratan sulfate (KS), and heparan sulfate (HS) have sulfate group modifications in their internal structures, bind to coreproteins as side chains varying lengths. GAG-modified protein molecules are called proteoglycans (PG).3)

Acidic Polysaccharides (Glycosaminoglycans)

Hyaluronic Acid Sodium Salt from Bacteria, and Dermatan Sulfate Sodium Salt

 
Product No.Product NameMain Chain linkages Constituent Monosaccharides
H1791Hyaluronic Acid Sodium Saltβ1-4GlcAβ1-3GlcNAcGlcNAc, GlcA
D3672Dermatan Sulfate Sodium Saltβ1-4IdoAβ1-3GalNAc(4S)GalNAc(4S), IdoA
C0335Chondroitin Sulfate Sodium Saltβ1-4GlcAβ1-3GalNAc(4S or 6S)GalNAc(4S or 6S), GlcA
H0393Heparin Sodium Saltα1-4GlcA or IdoA(2S)β1-3GlcNAc(NS, 3S, 6S)GlcNAc(NS, 3S, 6S), GlcA, IdoA(2S)

‡Since polysaccharides are heterogeneous compounds, representative main chain linkages and constituent monosaccharides are shown. And the sulfate group in paren thesis is the OH position that can be introduced.

 

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Chemically Modified Polysaccharides (Sulfated Polysaccharides)

Sulfated polysaccharides are known as multifunctional polysaccharides, that are related in physiological functions on the cell surface in vivo. These polysaccharides have supportive effects of viral infections. It has been reported that chemical mimics of sulfated polysaccharides inhibit viral adhesion during infection step.4)

化学修飾多糖(硫酸化多糖)

ヒアルロン酸-高硫酸化

 
Product No.Product NameMain Chain linkages Constituent Monosaccharides
H1739Hyaluronic Acid, High-Sulfatedβ1-4GlcA(2S, 3S)β1-3GlcNAc(4S, 6S)GlcNAc(4S, 6S), GlcA(2S, 3S)
D5144Dextran Sulfate SodiumGlc(2S, 3S, 4S)α1-6Glc(2S, 3S, 4S)Glc(2S, 3S, 4S)

‡Since polysaccharides are heterogeneous compounds, representative main chain linkages and constituent monosaccharides are shown and the sulfate group in paren thesis is the OH position that can be introduced.

 

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Other Chemically Modified Polysaccharides

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