Glycoscience

N-Acetyl-L-talosaminuronic acid is a natural product that has been shown to have anti-inflammatory activity in experimental models of inflammatory bowel disease. N-Acetyl-L-talosaminuronic acid inhibits the production of proinflammatory cytokines, such as tumor necrosis factor alpha (TNFα), by binding to TNFα receptors on the surface of cells. This can be attributed to its ability to inhibit ATP levels and reduce oxidative stress, which are both factors that contribute to inflammation. N-Acetyl-L-talosaminuronic acid also has been shown to inhibit inflammatory responses in human monocytes and neutrophils. It binds specifically to her2+ breast cancer cells and inhibits their growth in culture. Furthermore, it has been shown to have cytotoxic effects on bladder cancer cells and can be used for the treatment of bladder cancer.

2-C-Hydroxymethyl-D-ribose is a sugar that has been found in the cell wall of Mycobacterium tuberculosis. It is also found in some other bacteria, such as Streptomyces coelicolor. 2-C-Hydroxymethyl-D-ribose may be involved in the synthesis of glycan and may have a role in the molybdenum cofactor biosynthesis pathway. This molecule has been shown to have acidic properties, which are most likely due to its hydroxyl groups. The 13C NMR spectrum for this compound shows three peaks at δ H = 138.2, 144.3, and 154.5 ppm corresponding to the ribofuranoside moiety. The skeleton of this molecule was rationalized by attaching an acetaldehyde group to the 2'-hydroxyl group on position C2 of ribose, which is consistent with the observed 13C NMR spectrum. This molecule has

1-D-4-O-Methyl-myo-inositol is a compound that belongs to the group of biological compounds. It has been shown to have hypoglycemic effects in a model system and to inhibit 3t3-l1 preadipocyte differentiation. This compound also inhibits the activity of enzymes involved in metabolic pathways, and has an effect on lipid metabolism in kidney beans. 1-D-4-O-Methyl-myo-inositol has been shown to have antiobesity properties as well as antihyperglycemic activities.

D-Cellotetraose tetradecaacetate is a complex carbohydrate that consists of a single sugar, D-cellotetraose. It is made up of four glucose molecules attached to each other by glycosidic bonds. The modification of this carbohydrate can be done by methylation and glycosylation. The synthesis of this molecule can be custom-made, as it is not found in nature. This product is high purity and has a CAS number: 83058-25-7.

2,3,5-Tri-O-benzyl-b-D-ribofuranose is a synthetic monosaccharide that is used in the synthesis of complex carbohydrates such as glycosylation and polysaccharides. One use for this chemical is to modify the sugar moiety with methyl groups, yielding 2,3,5-tri-O-methyl b-D-ribofuranose. This modification helps prevent the sugar from being metabolized by enzymes in the body. The chemical can also be fluorinated to yield 2,3,5-trifluoro b-D-ribofuranose.

A linear β-(1,4)-galactan from potato tubers. Other linear β-(1,4)-galactans have been isolated from lemon peel, potato tubers and Norwegian acacia gum.

Sucrose octabenzoate is a practically colorless, odorless, transparent, glass-like material which is compatible with a number of synthetic resins, such as polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate and cellulose acetate. Sucrose octabenzoate improves the hardness and gloss of these products and has also been found to be useful as a component of inks, adhesives, coatings and plastic objects.

1,3,5-Tri-O-benzoyl-a-D-ribofuranose is a modified carbohydrate. It is synthesized by the methylation of 1,3,5-tri-O-benzoyl-a-D-arabinopyranose followed by glycosylation with 3,6-dideoxyhexose. This compound has been used as a substrate in enzymatic studies to investigate the modification of carbohydrates by glycosylation and methylation and can be used for the synthesis of other saccharides.

α-D-Mannose-1-phosphate sodium is a synthetically made mannose phosphate. This compound is used in the synthesis of oligosaccharides and glycoproteins.

Isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside is a modification of an oligosaccharide. It has been synthesized and characterized by NMR spectroscopy. This carbohydrate is custom synthesized as a complex carbohydrate. It is also a synthetic carbohydrate. Isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside is used as a monosaccharide, in glycosylation, methylation, polysaccharides, and other sugar chemistry reactions. Isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside can be used for fluorination or saccharides.

1,2:3,4:5,6-Tri-O-isopropylidene-D-glycero-L-gulo-heptitol is a fluorinated monosaccharide that is synthesized from D-glucose. It is used as an experimental carbohydrate for glycosylation and modification reactions with other compounds. 1,2:3,4:5,6-Tri-O-isopropylidene-D-glycero-L-gulo-heptitol has a CAS number of 152400–59–1.

N- [(2R, 3R, 3aS, 9aR) - 2, 3, 3a, 9a- Tetrahydro- 3- hydroxy- 2- (hydroxymethyl) - 3a- methyl- 6H- furo[2', 3':4, 5] oxazolo[3, 2- a] pyrimidin-- 6- ylidene] -benzamide is a modified carbohydrate. It is methylated at the C2' position and contains saccharide chains with polysaccharides. The molecular weight of this compound is 458.97 g/mol. This compound can be used for custom synthesis and modification.

Iota-Carageenan is a gelling sulphated galactan extracted from red seaweed (typically Euchuma cottonii and Euchuma spinosum). The structure of all carrageenans consists of a strictly alternating masked repeating unit of (1,3) linked α-D-galactose and (1,4) linked β-D-galactose. The α-linked galactose occurs as a 3,6-anhydro-2-sulphate unit and the β-linked sugar occurs as the 4-sulphate.
The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

2-Acetamido-2,6-dideoxy-D-galactose (2ADG) is a structural analogue of the natural monosaccharide 2,6-dideoxy-D-galactose. It has been shown to have an antimicrobial effect against aerobacter aerogenes in vitro. 2ADG is metabolized by glycosidases and methyl glycosides to form 1,4-anhydro-2,3,4,6 tetraacetamido-2,4,6 dideoxy D galactose. This compound inhibits the growth of bacterial strains that are resistant to polymyxin b., such as Pseudomonas aeruginosa. The inhibition of these bacteria is due to the inhibition of the synthesis of their outer membrane lipopolysaccharides by 2ADG. The antibacterial activity is also attributed to its ability to inhibit the metabolism of glycan molecules in some bacteria

NGA2F Glycan is a complex carbohydrate that is synthesized by the enzymatic transfer of an N-acetylgalactosamine (GalNAc) residue to a serine or threonine residue on protein. It is modified with methylation, Click modification, and fluorination. NGA2F Glycan has two binding sites for 2-AB labelled monosaccharides. The glycosylation site is located at the non-reducing end of the molecule, while the oligosaccharide site is located at the reducing end of the molecule.

Man-5 N-glycan is a glycan that is synthesized by the enzyme mannosyltransferase. This glycan contains five mannose residues, one galactose residue, and one N-acetylglucosamine residue. The Man-5 N-glycan is found in eukaryotes, which are organisms whose cells have nuclei and membrane bound organelles. It is often found on the surface of cells or in secretions such as mucus or saliva. Man-5 N-Glycans are involved in cell signaling and may play a role in bladder cancer development. They are also used to generate monoclonal antibodies for diagnostic purposes.

2-Deoxy-2-fluoro-D-arabinofuranose is a purine nucleoside that is used in the diagnosis and treatment of herpes simplex virus infection. It inhibits viral replication by competitively inhibiting acycloguanosine, an enzyme that catalyzes the conversion of 2’-deoxyguanosine to deoxyadenosine. 2-Deoxy-2-fluoro-D-arabinofuranose has been shown to be active against cancer cells and can be used as chemotherapeutic agent. This drug may also be used for the diagnosis of cancer by detecting the presence of activated T cells in patients with tumor necrosis factor α (TNFα) receptor gene polymorphism.

Isolated from ivory-nut mannan hydrolysates

6-Deoxy-L-allitol is a white crystalline solid that melts at 122°C. It has an amorphous character and may be present as a mixture of rotations, form, and crystalline polymorphs. 6-Deoxy-L-allitol can be oxidized to its diol derivative by hydrogen peroxide or sodium periodate. This compound is soluble in water, methanol, and acetone. The molecular weight of this compound is 179.06 g/mol.

a-D-Glucuronic acid-1-phosphate is a substrate for alkaline phosphatase. It hydrolyzes phosphate esters and modifies inorganic phosphate, including pyrophosphate. It also catalyzes the hydrolysis of nucleotide monophosphates such as NADPH and UDPglucose to their respective diphosphates. This enzyme is not inhibited by inorganic phosphate, phosphatase, NADP+, or UDP-.

Neutral pentasaccharide naturally present in human breast milk

Starch consists of two polysaccharides, amylose and amylopectin and represents approximately 20-25% of the total polysaccharide content in starch. Amylose molecules consist of single mostly unbranched chains of 500-20,000 α-(1->4)-D-glucose residues dependent on source (e.g. wheat, rice, potato, tapioca, etc). Amylose can form an extended shape (hydrodynamic radius 7-22 nm) but generally tends to wind up into a rather stiff left-handed single helix or form even stiffer parallel left-handed double helical junction zones. Hydrogen bonding between aligned chains causes retrogradation and releases some of the bound water (syneresis). The aligned chains may then form double stranded crystallites that are resistant to amylases. These possess extensive inter- and intra-strand hydrogen bonding, resulting in a fairly hydrophobic structure of low solubility. The amylose content of starches is thus the major cause of resistant starch formation.

L-Guluronic acid sodium is a monosaccharide that plays a crucial role in cardiac health. It is involved in the uptake and utilization of polyene carbohydrates, carotenoids, and fatty acids by human myocardial cells. L-Guluronic acid sodium has been shown to enhance the bioavailability of these essential nutrients, promoting optimal heart function. Additionally, this compound acts as a reactive analog, mimicking the effects of certain molecules involved in mammalian cell signaling pathways. This unique property makes L-Guluronic acid sodium a potential therapeutic agent for various cardiovascular conditions and may have implications in other areas such as stent technology and cancer research.

Bearberry has been used for centuries to treat various disorders of the urinary tract and prostate. The active ingredient in bearberry is a flavonol glycoside called arbutin, which is converted to hydroquinone during metabolism. As an antioxidant, hydroquinone inhibits the oxidation of LDL cholesterol and may reduce the risk of atherosclerosis. Hydroquinone has also been shown to have anti-inflammatory properties in rat liver microsomes and tissue culture, inhibiting prostaglandin synthesis by blocking cyclooxygenase activity. In vitro, bearberry extracts have been shown to inhibit bacterial growth on agar plates with pH levels from 4-7 and at concentrations between 0.1-1%. It was found that bearberry extracts were most effective against Pseudomonas aeruginosa strains, with MIC values ranging from 2-4 mg/mL. Bearberry extract was observed to be more effective than ampicillin against these strains in a chromatographic assay.

Dextran is α-(1,6)-linked α-D-glucan produced by fermentation of Leuconostoc mesenteroides via the action of the enzyme dextransucrase on sucrose. The main use for native dextran is as a blood plasma extender in blood transfusions. A complex of iron with dextran, known as iron dextran, is used as a source of iron to baby piglets which are often anaemic at birth.

This beta-cyclodextrin (β-CD) derivative is a functionalized cyclic oligosaccharide composed of seven glucose units, characterized by a hydrophilic exterior and a lipophilic cavity (bigger than α-CD and smaller than γ-CDs), which allows it to encapsulate various guest molecules. This structural feature facilitates its use in multiple applications, including pharmaceuticals, food enhancement, and cosmetics. In the pharmaceutical industry, it enhances the solubility and stability of poorly water-soluble drugs, improving their bioavailability and efficacy while also masking unpleasant tastes. The food sector utilizes it as a stabilizer for flavors, colors, and nutrients, extending shelf life by protecting sensitive ingredients from degradation. In cosmetics, it serves as a complexing agent for fragrances and active components, ensuring their stability and controlled release. Its use expands to many other fields, including nanotechnology for drug delivery systems, environmental remediation for extracting organic pollutants, textiles for slow-release fragrances, and analytical chemistry for chiral separation.

L-Gluconic acid calcium salt is a white crystalline powder. It is soluble in water and slightly soluble in alcohol. The structure of this compound has not been fully elucidated, but it is known to be a modification of L-gluconic acid, which is a monosaccharide. This product can be used as a biochemical reagent for the synthesis of oligosaccharides and polysaccharides.