Oligosaccharides

Tetra-guluronic acid sodium salt (1,4-linked α-L-sodium guluronotetraose) is one of a number of oligosaccharides obtained from alginate, a polysaccharide from brown seaweeds. It contains blocks of: repeating mannuronic acid sequences (M-M-M-M etc), repeating guluronic acid sequences (G-G-G-G etc), and alternating M-G-M-G sequences. This oligosaccharide can be released by acid hydrolysis and a number of biological activities have been discussed in a recent review.

Applications: Laninamivir (L174000) prodrug; a novel long-acting neuraminidase inhibitor. References Neumann, G., et al.: Nature, 459, 931 (2009), Yamashita, M., et al.: Antimicrob. Agents Chemother., 53, 186 (2009),

Lipopolysaccharides are a heterogeneous group of molecules that include endotoxins, lipid A, and core oligosaccharide. They are released from the cell wall of gram-negative bacteria as a result of bacterial lysis. Lipopolysaccharides are potent activators of immune cells, inducing the secretion of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β). TNF-α is also known to induce the production of other pro-inflammatory cytokines including IL-6, IL-8, IL-10, and IL-12. Lipopolysaccharides have been shown to cause liver damage in animals by increasing plasma alanine aminotransferase levels. This may also be due to their ability to induce the production of malondialdehyde and c-reactive protein.

3-(Hepta-O-acetyl-b-lactopyranosyl)thio-propanoic acid is a synthetic glycosylate that has been subjected to a click reaction with 4-iodo-1,1,3,3,-tetramethyluronium tetrafluoroborate. This glycoside has a purity of >98% and is offered at a price of $6.00/g.

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4,6-O-Benzylidene-D-maltose is an oligosaccharide that is a high purity custom synthesis. It has a Click modification and can be synthesized using the Fluorination and Glycosylation reaction. 4,6-O-Benzylidene-D-maltose is soluble in water and ethanol, but insoluble in ether. This product is listed as CAS No. 93417-41-5 and has a Methylation modification. 4,6-O-Benzylidene-D-maltose is also found in saccharides, carbohydrates, and complex carbohydrates.

GM1-biotin ganglioside (sodium salt) has a core tetrasaccharide structure (Galβ1,3GalNAcβ1,4Galβ1,4Glc) with sialic acid linked α2,3 to the inner galactose residue, ceramide linked β to position 1 on the reducing terminal glucose residue, and biotin to position 5 on sialic acid (Ledeen, 2009). GM1 ganglioside is abundant in all mammalian brains where it covers 10%-20% of the total ganglioside mixture. It is found in epithelial membranes and is a key element for bacterial toxicity and viral infection as it is the intestinal receptor for the cholera toxin, the B-subunits of heat-labile toxin, rotavirus, and simian virus 40. GM1 ganglioside functions as a neurotrophic and neuroprotective compound, and has been used therapeutically for diabetic and peripheral neuropathies. GM1 ganglioside also has the ability to bind amyloid-β proteins and is involved in Alzheimer’s pathogenesis (Chiricozzi, 2020).

a1-3,a1-6-Mannotriose-BSA is a carbohydrate that is synthesized by the modification of maltotriose with a fluorinated alcohol. It is an oligosaccharide made up of three glucose units linked together in a 1,3 configuration and one glucose unit linked together in a 1,6 configuration. The molecular weight of this carbohydrate is 793 Daltons. This product has been shown to be high purity and custom synthesis for use in research.

3-O-Acetyl-1,6-anhydro-2-azido-2',3'-di-O-benzyl-4',6'-O-benzylidene-2-deoxy-b,D cellobiose is a fluorinated oligosaccharide that can be customized for a variety of applications. The sugar unit contains an acetyl group on the C1 position and an azido group at the C2 position. This compound has been subjected to click chemistry in order to form a covalent bond with 4,6'-O-benzylidene 2,3'-dideoxy b,D cellobiose.

Lewis Y-O-(CH2)8-biotin is a carbohydrate with the chemical formula (CHO)(CO)3OH. It is a methylated and glycosylated oligosaccharide that has been custom synthesized for use in biotechnology applications. Lewis Y-O-(CH2)8-biotin has been fluorinated at the C5 position to improve its stability and prevent hydrolysis, which may be due to its high purity. This carbohydrate is not commercially available and must be custom synthesized.

Applications β-Sitosterol and β-sitosteryl-β-D-glucoside were isolated as analgesic constituents from the leaves of Mentha cordifolia Opiz. References Tanaka, et al.: J. Biochem., 17, 483 (1933), Nigro, N.D., et al.: J. Natl. Cancer Inst., 69, 103 (1982),

Applications Uridine-2-13C-1,3-15N2 is labelled Uridine (U829910) which is a nucleoside widely distributed in nature. Uridine is one of the four basic components of ribonucleic acid (RNA) References Lorine, P., et al.: J. Biol. Chem., 178, 439 (1949); Grakoui, A., et al.: J. Virol., 63, 5216 (1989); Strauss, J., et al.: Microbiol. Rev., 58, 491 (1994); Lin, Y., et al.: Virology, 292, 78 (2002);

NA2F Glycan is a custom synthesis that is used in the identification and quantification of methylated polysaccharides. It is a synthetic modification of a natural glycosylation reaction. The NA2F Glycan is synthesized by 2-AB labelled Methylation, saccharide, Polysaccharide, CAS No., Click modification, Modification, Oligosaccharide, Custom synthesis, Glycosylation, High purity, Carbohydrate, sugar, Synthetic, Fluorination with high purity and complex carbohydrate. This product can be used in glycobiology research as a methylation-sensitive probe for the detection of methylated polysaccharides such as glycoproteins and glycolipids.