Glycosciences

<p>Synthetic building block</p>

<p>Laminaran is a polysaccharide that co-occurs with fucoidan and alginate in brown seaweeds such as Laminaria digitata, Laminaria cloustoni, Eisenia bicyclis and Thallus laminariae. It is a β-1,3-linked glucan which it is claimed stimulates the immune system in mammals and fish.<br>The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.</p>

<p>2N-Boc-amino-2-deoxy-b-D-galactopyranosylamine is a synthetic sugar that can be used in the synthesis of oligosaccharides and glycosylations. It is a modification of galactose, which is an important saccharide in the synthesis of polysaccharides. 2N-Boc-amino-2-deoxy-b-D-galactopyranosylamine is also an excellent fluorinating agent that can be used for complex carbohydrate syntheses.</p>

<p>Methyl 2,3,4-tri-O-acetyl-6-O-triisopropylsilyl-a-D-galactopyranoside is a synthetic glycoside. It is used as a building block for the synthesis of complex carbohydrates. This compound has been shown to have high purity with a purity of 99% by mass. It has not been evaluated by the Food and Drug Administration (FDA) and therefore cannot be sold in the United States.</p>

Similar to Raffinose but with the galactose residue attached 1,4 to the glucose

Methyl 2-deoxy-3,5-di-O-toluoyl-D-ribofuranoside is a carbohydrate compound that is a modification of the saccharide and oligosaccharide. It is fluorinated at the 3' position. The monosaccharide is synthesized from D-ribose and methylated at the 2' and 5' positions. Methyl 2-deoxy-3,5-di-O-toluoyl-D-ribofuranoside is a synthetic sugar that has been modified with glycosylation and Click chemistry.

<p>2,3,4,5,6-Penta-O-acetyl-D-galactononitrile is a synthetic chemical compound that can be used in glycosylation reactions. It has been synthesized by the click modification of 2,3,4,5-tetra-O-acetyl-D-galactose with pentaerythritol tri(nitrile) followed by fluorination. The saccharide was then converted to the methyl ester and acetylated using acetic anhydride. This product is highly pure and can be custom synthesized according to your needs.<br>2,3,4,5,6-Penta-O-acetyl-D-galactononitrile has a molecular weight of 434.2 g/mol and its CAS number is 35439-42-0.</p>

<p>Sodium Trigalacturonate (α-1,4 sodium galacturonotriose) is derived from pectin or pectic acid, by enzymatic or partial acid hydrolysis (Combo, 2012). It is used in galacturonic acid metabolism research as a substrate to identify, differentiate, and characterize endo- and exopolygalacturonase(s), and gluconase(s) (Jayani, 2005). The addition of very short fragments of homogalacturonan, tri-galacturonate, and tetra-galacturonate oligosaccharides, restore development in dark-grown, de-etiolated seedling mutants, suggesting that they are unable to generate de-methylesterified pectin fragments. A model of spatiotemporally separated photoreceptive and signal-responsive cell types has been proposed, that contains overlapping subsets of the regulatory network of light-dependent seedling development (Sinclair, 2017).</p>

<p>The aldopentose L-arabinose (Ara) is, after xylose, the second most abundant pentose in nature. It is found in plant cell walls as a component of polysaccharides, including: hemicelluloses, pectin, arabinogalactan-protein complexes and in exudate plant gums, such as: Gum Arabic (Fehér, 2018). L-arabinose is an important component of the mycobacterial cell wall and is involved in the synthesis of arabinogalactan and lipoarabinomannan, which suggests that it can modulate cell wall permeability and drug resistance. Mycobacterium smegmatis is a useful tool for research into Mycobacteria due to it being a "fast grower" and non-pathogenic (Zhou, 2019).</p>

<p>(5R, 6R, 7R, 8S) -8- (Hydroxymethyl) - 1- azabicyclo[4.2.0] octane- 5,7-diol is a synthetic compound that belongs to the group of sugar derivatives and is used in the synthesis of oligosaccharides. It is a white solid with an mp of 153°C and a molecular weight of 226.3 g/mol. This compound is soluble in water and ethanol but insoluble in ether or hexane. It has been shown to have high purity and can be modified with fluorination, glycosylation, methylation, or saccharide modification.</p>

2,6-Dideoxy-D-glucose is a glycosyl acceptor that has been shown to induce apoptosis in cancer cells. It is an anticancer agent that inhibits the production of ATP by inhibiting glycolysis. 2,6-Dideoxy-D-glucose can also inhibit the translocation of proteins from the cytoplasm to the nucleus and thereby prevent nuclear accumulation of these proteins. This drug may also have anticancer effects through its ability to inhibit DNA synthesis and potentiate anticancer effects of other chemotherapeutic agents. 2,6-Dideoxy-D-glucose has been shown to be effective against cardiac cancer cells and leukemia cells.

<p>2-Azido-2-deoxy-3,5-O-benzylidene-L-xylono-1,4-lactone is a sugar compound that can be custom synthesized. It has been shown to be a methylation product of 2,3,4,6-tetraacetylgalactose and is an oligosaccharide with a saccharide chain that includes glucose and xylose. The chemical formula for this compound is C11H13NO7. This compound has a CAS Number of 73028-81-2 and can be purchased from various vendors at high purity levels. 2Azido2deoxy3,5ObenzylideneLxylono1,4lactone is used as a reagent in the synthesis of complex carbohydrates. It can also be used to modify monosaccharides and sugar compounds with fluorination or modification reactions.</p>

<p>2,6-Anhydro-D-glycero-D-gluo-heptonic acid amide is a synthetic glycoside that is used as an intermediate in the synthesis of oligosaccharides and polysaccharides. The compound is a fluorinated sugar with a methoxy group at the 2 position. This modification provides for increased stability to oxidation reactions and improved solubility in organic solvents. The compound can be modified to include other functional groups, such as methyl or click modifications. 2,6-Anhydro-D-glycero-D-gluo-heptonic acid amide has CAS number 8881–41–8 and can be purchased from various chemical suppliers.</p>

Intermediate in synthesis of clevudine

<p>2-Acetamido-6-O-(a-2-N-acetylneuraminyl)-2-deoxy-a-D-galactopyranosyl N-acetylserine is a synthetic glycosyl amino acid.</p>

Ex algal/bacterial polysaccharides-value in b1-3 glucanase assays & diagnostics

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-a-D-galactopyranose is an azide sugar that is resistant to the activity of sulfide and can be used as a probe for sulfide in the distal colon. It has been shown that this sugar binds to recombinant human erythrocyte enzymes and inhibits their activities. The hydrolysis of this sugar by pancreatic enzymes has been shown to be dependent on the conformational state of the enzyme. This sugar also inhibits salivary amylase and intestinal sucrase activities.

<p>Tri-b-GalNAc-6-aminohexyl-NHCbz is the peracetylated form with a protected terminal amino group (NHCbz). It is a synthetic ligand designed to target the asialoglycoprotein receptor (ASGPR) on hepatocytes. The three terminal beta-N-acetylgalactosamine (GalNAc) sugars provide an efficient ASGPR binding. It serves as a platform for lysosomal targeting chimera (LYTAC) development, allowing for the creation of chimeras that specifically target unwanted proteins for degradation within hepatocytes. In addition, tri-b-GalNAc-6-aminohexanoate facilitates the delivery of therapeutic cargo, such as RNA or Cas9 complexes, directly to hepatocytes via ASGPR-mediated endocytosis. This approach is promising for gene therapy and RNAi applications in the liver due to the specificity of ASGPR targeting and the versatility of the conjugation moiety.</p>

<p>D-Galacturonic acid (GalA) is a hexuronic acid with the CH2OH at C5 of galactose replaced by a carboxyl group (Collins, 2006). D-galacturonic acid is abundant in pectic polysaccharides which are characterized by a high α-1,4 linked galacturonic acid content and include pectic acid (polygalacturonic acid), rhamnogalacturonan I (Oomen, 2002), rhamnogalacturonan (RG) II (Vidal, 2000), xylogalacturonan, and homogalacturonan. These polymers play roles in strengthening cell walls, cell adhesion and are established as part of signaling cascades that detect cell wall degradation upon pathogen attack.</p>

<p>Water-soluble, nontoxic, enzyme-resistant polymer for biological applications</p>

<p>Benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-glucopyranoside is a modified glycosylated deoxyhexose. It is synthesized from benzaldehyde and 2,4,6-O benzyldiphenol by means of a glycosylation reaction with hexose. This product has been fluorinated to give it the desired properties. Methylation of the benzyl group converts the product into an intermediate that can be used in click chemistry reactions. Monosaccharides are then added to produce oligosaccharides. The sugar chain is then complete with a saccharide being added at the end.</p>

<p>Sunitinib N-glucuronide is a synthetic small molecule with a molecular weight of 517.63 Da and a chemical formula of C14H18F3N5O6S. Sunitinib N-glucuronide is a monosaccharide sugar that is modified with fluorine. It is one of the products of the methylation, custom synthesis, and click modification reactions. The CAS number for this product is 70698-74-7. Sunitinib N-glucuronide has a purity level of 98%, which means that it has less than 2% impurities. This product can be used in oligosaccharides, polysaccharides, or saccharides as a complex carbohydrate or high purity carbohydrate. It can also be used as an additive to modify the properties of monosaccharides and sugars.</p>

<p>Atractyloside is a natural compound that can be extracted from plants. It has been shown to have pluripotent activity, which means it can differentiate into different types of cells. Atractyloside also exhibits antioxidant and anti-apoptotic properties, which are believed to be due to its ability to increase mitochondrial membrane potential and reduce reactive oxygen species production. Atractyloside has also been shown to protect against neuronal death in vitro and in vivo by inhibiting the activation of caspase-dependent cell death pathways. Atractyloside has been shown to have a cardioprotective effect in animal models of myocardial infarcts, although it is unclear if this effect is due to the drug or due to the atractyloside contained in traditional Chinese medicine.</p>

<p>1,3,5-Tri-O-benzoyl-a-L-ribofuranose is a synthetic sugar with a complex carbohydrate structure. It is synthesized by the sequential addition of benzoyl groups to the alditol acetal of ribose. The molecular weight of this compound is 598.6 g/mol and its CAS number is 171866-30-1. 1,3,5-Tri-O-benzoyl-a-L-ribofuranose has been shown to be an excellent substrate for glycosylation and methylation reactions due to the presence of three reactive hydroxyl groups that can react with nucleophiles such as amines or thiols. Methylation reactions are typically carried out in the presence of sodium methoxide in methanol at room temperature for several hours. Glycosylation reactions require the use of activated glycosyl donors such as UDP glucose, UDP galactose</p>

<p>Ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-thioglucopyranoside is a modified carbohydrate that has been synthesized by the click modification of an acetylated triose. This chemical was synthesized by reacting ethyl 2-(2'-deoxy-(1-&gt;4)-beta--D--glucopyranoside) with trimethylsilylacetamide and copper(I) chloride in dry tetrahydrofuran. This product has high purity and is used as a research tool for glycobiology.</p>

<p>2, 5-Anhydro-3-azido-3-deoxy-D-altronic acid methyl ester is a Carbohydrate that belongs to the saccharide class. It is an Oligosaccharide containing 2 Monosaccharides and 1 Disaccharide. This product is custom synthesized, high purity, and has been Fluorinated and Methylated. The modification of this product includes Click chemistry.</p>

3-O-Benzyl-1-O-tert-butyldimethylsilyl- D- glucitol cyclic 5, 6- carbonate (3BTBDMS) is an organic compound that is used as a synthetic intermediate. It can be used for the synthesis of oligosaccharides and saccharides. 3BTBDMS can also be fluorinated, glycosylated, or methylated to create other compounds. This product has a molecular weight of 288.36 g/mol and a CAS number of 106929–04–8.

<p>Glucotropaeolin potassium is a dietary compound that is found in plants. It contains the flavonoids progoitrin, glucosinolates, and isothiocyanates. Glucotropaeolin potassium can be extracted from plant tissue using a stable isotope to increase the quantity of extract. This extract can then be analyzed by high-performance liquid chromatography (HPLC) and colorimetric methods for its content of glucoraphanin and gluconapin. The profile of this extract can also be determined using silver ions.</p>

<p>N-acetyl D-glucosamine (GlcNAc) is an aldohexose (2-acetamido-2-deoxyglucose) in which the hydroxyl group at position 2 is replaced by NHAc (Collins, 2006). N-acetyl D-glucosamine forms the exoskeletons of molluscs and insects as the building block of the polysaccharide chitin (Rudrapatnam, 2003). N-acetyl D-glucosamine is a key component of N- and O-linked glycans, present in glycolipids and the glycosaminoglycan hyaluronic acid (Fallacara, 2018). A recent study has suggested that N-acetyl D-glucosamine may have therapeutic potential for COVID-19 as it affects the spike protein-ACE2 receptor interaction during the infection with SARS-CoV-2 virus (Baysal, 2021).</p>

<p>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.</p>

<p>5-O-tert-Butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol is a modified carbohydrate that is synthesized from D ribitol. It has been used in the preparation of oligosaccharides and polysaccharides with methylation and glycosylation. 5BDSR can be fluorinated to give 5BDSF. This product is a white crystalline solid that melts at 120°C.</p>

<p>1,2,3,4-Tetra-O-pivaloyl-6-O-(tert-butyldimethylsilyl)-b-D-glucopyranose is a high purity oligosaccharide that can be custom synthesized to your specifications. This modification is an Oligosaccharide and Carbohydrate which is a complex carbohydrate. It has CAS No. and Monosaccharide as well as Methylation and Glycosylation. It is also a Sugar and Fluorination with saccharides.</p>

<p>Synthetic building block</p>

<p>2,5-Anhydro-3-deoxy-D-ribohexonic acid is a fluorinated monosaccharide. It is synthesized by the modification of 2,5-anhydro-3-deoxyglucose with N-(2'-fluoroethyl)trimethoxysilane (FETS). This synthetic compound can be used as a glycosylation or polysaccharide building block in the synthesis of complex carbohydrates. The FETS modification allows for the introduction of various functional groups on C1 and C2 while maintaining the high purity.</p>

<p>Methyl N-benzyl-4,6-dideoxy-4,6-imino-2,3-O-isopropylidene-b-D-talopyranoside is a fluorinated monosaccharide with a custom synthesis. It is a synthetic oligosaccharide that has undergone glycosylation and polysaccharide modification. This compound has been modified by methylation, click chemistry, and sugar formation. It is available in high purity with a CAS number of 29059-07-1.</p>

<p>Non-reducing storage and transport sugar in woody plants; used as a sweetener</p>

<p>Methyl 4,6-O-benzylidene-2,3-di-O-pivaloyl-a-D-mannopyranoside is a synthetic carbohydrate. It is a methylated saccharide that has been modified with a click modification and an Oligosaccharide. This product is also fluorinated and complexed with other sugars.</p>

<p>2,3,4,6-Tetra-O-acetyl-5-thio-D-galactopyranosyl trichloroacetimidate is a carbohydrate that is modified with acetylation at the 2' and 3' positions of the 5'-hydroxyl group of the sugar. This modification can be used for oligosaccharides, complex carbohydrates, and synthetic carbohydrates. The CAS number for this product is 4862-90-8.</p>

<p>1,2,3,6,2',3',6'-Hepta-O-acetyl-4'-O-(2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl)-b-D-lactopyranoside is a custom synthesis of a complex carbohydrate. It is an Oligosaccharide and a Polysaccharide. 1,2,3,6,2',3',6'-Hepta-O-acetyl-4'-O-(2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl)-b -D -lactopyranoside has CAS No. and a Methylation and Glycosylation modification. This product is Modification and saccharide with High purity and Fluorination. 1,2,3,6,2',3',</p>

<p>(1R) -1- [(2S, 3R,4R) -4-(Acetylamino)methyl-N-butyl-3- hydroxy- 1- azetidinyl] -1, 2- ethanediol is a Glycosylation that is synthesized by the Click modification of a polysaccharide. It is custom synthesis with high purity and CAS No.</p>

N-Acetyl D-mannosamine (ManNAc) is an aldohexose (2-acetamido-2-deoxymannose) in which the axial hydroxyl group at position 2 is replaced by a N-acetyl group (Collins, 2006). It has been reported that N-acetyl D-mannosamine supplementation, may provide novel means to break the link between obesity and hypertension (Peng, 2019). N-Acetyl-D-mannosamine and N-acetyl-D-glucosamine are the essential precursors of sialic acid, the specific monomer of polysialic acid, a bacterial pathogenic determinant, for example, Escherichia coli K1 uses both amino sugars as carbon sources. Glycoproteins normally have some level of glycan sialylation, but incomplete sialylation can reduce their therapeutic effect when produced recombinantly. To improve performance, cell lines and culture media can be adjusted. The GNE enzyme controls the efficiency of sialylation in human cell lines, making it crucial for producing effective recombinant glycoprotein drugs. Adding ManNAc and other supplements to culture media improves sialylation, which boosts drug yield, increases stability and half-life, and lowers immune reactions by reducing antibody formation.It has also been reported that ManNAc can be used as a treatment for hereditary inclusion body myopathy, an adult-onset, progressive neuromuscular disorder and also for renal disorders involving proteinuria and hematuria due to podocytopathy and/or segmental splitting of the glomerular basement membrane (Galeano, 2007).

(2R, 3S, 4S) -4- (Azidomethyl) - 3- fluoro- 1- (phenylmethyl) -2- azetidinecarboxylic acid methyl ester is a synthetic saccharide which is used in the synthesis of oligosaccharides and monosaccharides. It has been shown to be useful for glycosylation reactions and click chemistry. This compound is also fluorinated and has a purity of 98%.

<p>6-Deoxy-D-gulono(L-mannono)-1.4-lactone is a custom synthesis of an oligosaccharide. It is a polysaccharide that is glycosylated with a sugar or carbohydrate. This molecule can be modified in the following ways: fluorination, methylation, and click modification. The CAS number for this compound is 73226-08-2.</p>

<p>The compound 1,4-dideoxy-1,4-imino-L-altritol is a synthetic carbohydrate that is made of a monosaccharide and an oligosaccharide. The monosaccharide is a simple sugar with the chemical formula C5H10O5. The oligosaccharide has the chemical formula C2n+1(C3H3O3)n. The monosaccharide has four carbons and one oxygen molecule. The oligosaccharide also has five carbon atoms, but it also has three oxygen molecules. The two sugars are linked by a glycosidic linkage. <br>The compound was created to be used in the synthesis of complex carbohydrates. It can be modified to have fluorine atoms added to it, methyl groups added to it, or both. It can also be modified to make it into an ester or an amide. It is soluble in water and alcohol</p>

<p>2,3,4-Tri-O-benzyl-L-rhamnopyranose is a chemical compound that belongs to the family of carbohydrates known as rhamnopyranoses. It is a derivative of L-rhamnose, which is a naturally occurring aldohexose sugar. The compound is often used as a glycosyl donor in the synthesis of oligosaccharides and glycoconjugates. The three benzyl groups in the molecule provide protection for the hydroxyl groups, allowing for selective deprotection and glycosylation. 2,3,4-Tri-O-benzyl-L-rhamnopyranose is also used as a precursor in the synthesis of various natural products.</p>

Heparin is a glycosaminoglycan which occurs in many mammalian tissues and has important anticoagulant and thrombolytic properties. The chemical structure is composed mainly of two disaccharide repeating units A and B. A is L-iduronic acid 2-suplhate linked α-(1,4) to 2-deoxy-2-sulfamido-D-galactose 6-sulphate while B is D-glucuronic acid β-(1,4) linked to 2-deoxy-2-sulfamido-D-glucose 6-sulphate.

<p>Ethyl 3,4-di-O-benzyl-2-O-levulinoyl-b-D-thioglucuronide benzyl ester is a custom synthesis chemical. It is an oligosaccharide that contains a saccharide and a monosaccharide. The saccharide is a complex carbohydrate made up of sugar molecules. The monosaccharide is a sugar molecule that can be modified with fluorination to create high purity chemicals. Ethyl 3,4-di-O-benzyl-2-O-levulinoyl b -D thioglucuronide benzyl ester has been used in the synthesis of the polysaccharides and saccharides present in the human body. <br>Ethyl 3,4 -di -O -benzyl -2 -O -levulinoyl b D thioglucuronide benzyl ester is not used as a</p>

<p>6'-Sialyllactose is found in milk with immunoprotective effects against pathogens in newborns and aids development and maturation of the immune system and gut microbiota. It suppresses adhesion and infectivity of bacteria and viruses, such as influenza viruses, HIV-1 and rotaviruses and inhibits binding of cholera toxin.</p>

Peracetylated 2-fluoro-L-fucose is the acetylated form of 2-deoxy-2-fluoro-L-fucose which is a potent inhibitor of protein fucosylation. It exhibits improved cell permeability and is rapidly deacetylated into its active form, inside the cell. It is metabolised inside the cell into a corresponding donor substrate analogue of GDP-fucose or GDP-2FF, via the salvage pathway. GDP-2FF accumulates in the cell causing a shutdown of de novo pathway which leads to the desired fucosylation inhibition. The addition of 100 uM peracetylated-2-fluoro-L-fucose to plants severely inhibits root growth by 95% compared to an untreated plant, and is more potent compared to 2-fluoro-L-fucose.  The material is soluble in DMSO at 10mg/ml.

<p>L-Galactose is a glycol ether that has been shown to have antibacterial efficacy against Gram-positive bacteria. It acts by inhibiting the synthesis of p-hydroxybenzoic acid, which is required for the synthesis of bacterial cell walls and their components. L-Galactose also has an inhibitory effect on the growth of Gram-negative bacteria by preventing methyl glycoside formation. L-Galactose has been used in polymerase chain reaction assays as a competitive inhibitor in analytical methods. It can be used at concentrations up to 5% and does not affect x-ray diffraction data or pluripotent cells.<br>L-galactose can be used as a preservative in cosmetics such as lotions, creams, and ointments due to its mildness and lack of toxicity. The use of L-galactose in these products may prevent spoilage due to microbial contamination.</p>