Glycosciences

1,2,3,4-Tetra-O-acetyl-L-rhamnopyranose is an acetylated disaccharide that is glycosylated with mercuric triflate and glycoalkaloid acceptors. It has been shown to be a glycosylation coupling agent for theophylline in solanum species. 1,2,3,4-Tetra-O-acetyl-L-rhamnopyranose can also act as a steroidal glycoalkaloid acceptor and has been identified in Solanum species.

1,2,3-Tri-O-benzoyl-4,6-O-(4-methoxybenzylidene)-b-D-galactopyranose is a synthetic glycosylation product of 3,6-dideoxygalactose and 1,2,3,4,6-pentaacetyl bromide. It has been subjected to fluorination and methylation reactions. The compound has been found to be effective in the treatment of tuberculosis.

Tetra-mannuronic acid sodium salt (β-1,4-linked sodium mannuronotetraose) is one of a number of oligosaccharides obtained from alginate which is a polysaccharide in brown seaweeds containing: 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.  Oligosaccharides can be released using several methods (Lua, 2015; Yanga, 2004) and claims have been published that mannuronic acid oligosaccharides for example, can be effective in the prophylaxis and treatment of Alzheimer's disease, or for the prophylaxis and treatment of diabetes (USP 8835403B2, 2014).

Thiogalactose is a naturally occurring disaccharide that has been shown to have anti-inflammatory properties. It inhibits the production of inflammatory cytokines, such as tumor necrosis factor-α (TNF-α), and suppresses the growth of experimental colitis in mice. Thiogalactose also denatures fatty acids and prevents 3t3-l1 preadipocytes from undergoing cellular transformation. This compound also inhibits the uptake of bovine serum albumin by macrophages, which may be due to its alkylthio group. Thiogalactose has been shown to inhibit proliferation of cultured human cells, including monocytic leukemia cells, when used at concentrations less than 10 mM.

N-Acetyl-5-bromo-3-indoxyl-2,3,4-tri-O-acetyl-b-D-glucuronic acid methyl ester is a custom synthesis of an acetylated bromoglycoside. This compound is a synthetic modification of the natural product and has been shown to be effective against various bacteria. The synthesis of this compound can be achieved by the click reaction with methyl 2,2'-dithiopropionate and 5,5'-dimethoxytrityl chloride in the presence of trimethylsulfonium iodide. N—Acetyl—5—bromo—3—indoxyl—2,3,4—tri—O—acetyl--b--D--glucuronic acid methyl ester is also a monosaccharide sugar that is a carbohydrate with a high purity and modifies proteins at their active site. It also has

Monosialylated glycosphingolipid with an α1,2-fucosylated galactose at the nonreducing end. The moluecule is minimally expressed in healthy tissues but has high prevalence in some tumours such as small cell lung cancer (SCLC). Fucosyl-GM1 ganglioside is a potential tumour marker for SCLC and a potential antigen target for immunotherapy.

6'-Fucosyllactose is a fucosylated form of lactose, which is a complex carbohydrate. It is a custom synthesis and has been synthesized in high purity. 6'-Fucosyllactose has CAS No. 80756-86-1 and can be found as an oligosaccharide or polysaccharide. 6'-Fucosyllactose is a monosaccharide that has been methylated and glycosylated to increase its stability. The saccharides are modified with fluorination to make it more soluble in water and to improve its solubility in organic solvents.

N-(7-Oxadecyl)deoxynojirimycin is a chaperone protein. It belongs to the group of proteins that are deficient in patients with type 1 glycogen storage disease and can be used to treat this condition. N-(7-Oxadecyl)deoxynojirimycin has been shown to bind to the endoplasmic reticulum, thereby preventing the maturation of certain proteins and their transport into other cellular compartments. This agent also has a protective function in muscle cells by preventing protein degradation due to abnormal folding or misfolding. The long-term effect of N-(7-Oxadecyl)deoxynojirimycin on skeletal muscle is unclear, although it has been found to be beneficial in the short term for patients with type 1 glycogen storage disease.

Methyl-2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside is a sugar that is synthesized by the methylation of an alpha-D-mannopyranoside. This compound can be customized for any application and is available in high purity. It is used as a building block for polysaccharides and oligosaccharides. Methyl-2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside has been shown to have many applications including being used as a click modification substrate. The synthesis of this compound can be done by fluorination or glycosylation.

Sucrose dipalmitate is a pharmaceutical dosage form that is made of sucrose, a high-energy sugar, and palmitic acid. It has a low energy content and can be used as a diagnostic agent in nuclear medicine. Sucrose dipalmitate can be used as an emulsifier in the preparation of nanoemulsions. The particle size of sucrose dipalmitate can be adjusted to achieve the desired effect. In addition, this compound is used for the treatment of cardiac disease and other conditions such as high blood pressure and diabetes.

D-Glucuronic acid (GlcA) is D-glucose with position six oxidised to a carboxyl group (Collins, 2006). It is a common component of a number of gums and mucilages structurally related to pectins, where it is can be present as a terminal non reducing end residue (Renard, 1999). Glucuronic acid is also found in bacterial polysaccharides, such as, xanthan gum produced by Xanthomonas campestris (Faria, 2011), and in glycosaminoglycans, such as, heparan sulfate (Casale, 2020).

Polyguluronic acid is produced from alginates by partial hydrolysis and chromatography of brown algae such as Laminaria digitata, Ascophyllum nodosum and Fucus spp.
The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.MW is ca 6000 - 8000Da.poly-M levels are ca 3%

Sorbitol, also known as glucitol, occurs widely in plants, such as, the fruits of the Sorbus and Crataegus spp.  Commercially it is produced by the catalytic hydrogenation of glucose (Collins, 2006).  Sorbitol is approved as a sugar substitute with the E number 420 and has ‘generally recognized as safe’ status (GRAS) from the US Food and Drug Administration. It is about 60% as sweet as sucrose and is a mild laxative.  Sorbitol has a wide range of other functional properties, including: humectancy, plasticizing ability, non-cariogenicity, and good chemical stability in harsh conditions, such as, alkaline pH and heat. Toothpaste production is the second largest application of sorbitol, accounting for 50,000 tons a year in Western Europe alone.  Other important uses of sorbitol as a humectant, include: formulation of cough syrups, multivitamin preparations, emulsions, and suspensions (O’Neil, 2013).