Glycoscience

Used to determine composition and sequence of glucan-containing mixed linkages

Isolated from ivory-nut mannan hydrolysates

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.

N-Propanoyl mannosamine is a biochemical that belongs to the group of glycoconjugates. It is an intracellular messenger that modulates the concentration of intracellular calcium and controls the release of gamma-aminobutyric acid (GABA). N-Propanoyl mannosamine has been shown to stimulate axonal growth in cell culture, which is mediated by the polysialic acid receptor. This molecule also has a role in human osteoblast differentiation and bone formation.
N-Propanoyl mannosamine can be synthesized from dopamine and erythrose via a series of reactions involving acidification, oxidation, reduction, and decarboxylation. The synthesis of this molecule requires blood group O as an acceptor.

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.

D-Arabonic acid-1,4-lactone is a synthetic sugar that is modified to produce a variety of carbohydrates. This product can be used in the synthesis of oligosaccharides and monosaccharides. It is also used as a carbohydrate in the production of saccharide-based polymers, such as polysaccharides or polyols. This product has CAS number 2782-09-4 and a purity level of ≥99%.

1-Amino-1-deoxy-D-galactitol hydrochloride is a natural polymer that is found in many organisms, including bacteria and fungi. It can be obtained by enzymatic conversion of galactose, which is an epimer of glucose. 1-Amino-1-deoxy-D-galactitol hydrochloride has been shown to have viscosity properties that are similar to those of natural polymers. This compound also has the ability to form hydrogen bonds with other molecules. 1-Amino-1-deoxy-D-galactitol hydrochloride is produced by chemoenzymatic reactions and can be used as a substitute for natural polymers in certain applications (e.g., food industry).

D-ribono-1,5-lactone is a useful intermediate for the synthesis of bioactive compounds including antivirals.

Intermediate in the synthesis of tofogliflozin

2,4-Dideoxy-2,4-difluoro-D-glucose is a fluorinated glucose analog that has been synthesized to be used as an imaging agent for positron emission tomography (PET) and single photon emission computed tomography (SPECT). It is labeled with fluorine-18 and can be metabolically incorporated into the cellular glycolytic pathway. 2,4-Dideoxy-2,4-difluoro-D-glucose emits positrons that are detected by PET or SPECT cameras. The incorporation of 2,4-dideoxy-2,4-difluoro--D--glucose into the glycolytic pathway allows it to be used as a marker for positron emission tomography.

The chemical structure of Astragalus polysaccharide is complex and consists of an α-D-(1,4)-Glc and (1,6)-α-D-Glcp backbone, and a branch point at O-6. The molecular weight is approximately 3.01 × 105 Da from Mongolian Astragalus using low concentration of ethanol for precipitation and gel chromatography for purification. Spectral analysis results of 1H NMR and 13C NMR showed that the polysaccharide backbone has a 1,3-linked β-D-Gal residue and the branched portion has β-Glc, 1,6-linked α-Gal; 1,5-linked β-Xyl; 1,4-linked β-Gal; β-D-Gal, 1,2-linked α-Rha; and 1,2,4-linked α-Rha residues.

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.

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-(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.

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.

1,2,3,4-Tetra-O-acetyl-6-aminobenzoyl-6-deoxy-a-D-glucopyranoside is a fluorinated monosaccharide that is synthesized from 6-deoxyglucose through the glycosylation of 1,2,3,4,-tetraaminobenzoyl chloride. It is a white solid with a molecular weight of 242.1 g/mol and a CAS Number of 368737-85-0. This product has been modified with methylation and click chemistry to give it desired properties for use as an intermediate in the synthesis of complex carbohydrates.

Allyl alpha-D-glucopyranoside is an optical isomer of D-glucose that is used in the synthesis of a number of synthetic trisaccharides, including maltotriose. Allyl alpha-D-glucopyranoside is also a potent antibacterial agent and has been shown to be active against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. Allyl alpha-D-glucopyranoside has hydrophilic and hydrophobic properties, which makes it soluble in both water and organic solvents. This compound can also form stable complexes with metal cations such as sodium and potassium, making it useful for tissue culture experiments.

Iota-cyclodextrin (ι-CD) contains 14 glucose units. This cyclodextrin has potential applications in host-guest chemistry, particularly for large molecules or assemblies.

Carboxymethyl cellulose is used in food as a viscosity modifier, thickener, to stabilise emulsions and are found in gluten-free and reduced-fat products. It is also a constituent of toothpaste, laxatives, diet pills, water-based paints, detergents, textile sizing, and various paper products.  In laundry detergents, it is used as a soil suspension polymer. It is also used in pharmaceuticals as a thickening agent and in the oil-drilling industry as a viscosity modifier and water-retaining agent.