3082-96-0

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER
• Synonyms: 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER;1,2,3,4-TETRA-O-ACETYL-D-GLUCURONIC ACID METHYL ESTER;METHYL 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANOSIDURONATE;METHYL 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONATE;METHYL-1,2,3,4-TETRA-O-ACETYL-D-GLUCORONATE;METHYL 1,2,3,4-TETRA-O-ACETYL-D-GLUCURONATE;D-Glucopyranuronic acid, methyl ester, tetraacetate;1,2,3,4-Tetra-O-acetyl-D-glucuronidemethylester
• CAS NO: 3082-96-0
• Molecular Formula: C₁₅H₂₀O₁₁
• Molecular Weight: 376.31
• Product Categories: Carbohydrates & Derivatives
• Mol File: 3082-96-0.mol

Chemical Properties

• Melting Point: 103-105°C
• Boiling Point: 412.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER(3082-96-0)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER(3082-96-0)

Safety Data

• Hazardous Substances Data: 3082-96-0(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER is used as an intermediate in organic synthesis for the production of various complex organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER is used as a key component in the development of novel drug candidates. Its versatile chemical structure enables the creation of new molecules with potential therapeutic applications, such as anti-inflammatory, anti-cancer, or anti-infective agents.
3. Used in Research and Development:
1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER is also utilized in research and development laboratories for the study of carbohydrate chemistry, glycobiology, and the development of new methodologies for the synthesis of complex carbohydrates and their derivatives. Its unique structure and reactivity make it an essential tool for understanding the role of carbohydrates in biological systems and the development of new therapeutic strategies.
4. Used in Material Science:
In the field of material science, 1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER can be employed as a component in the development of advanced materials with specific properties, such as stimuli-responsive hydrogels, drug delivery systems, or biocompatible coatings for medical devices. Its ability to form hydrogen bonds and interact with other molecules makes it a promising candidate for the design of novel materials with tailored properties.

Upstream product

• 82228-14-6 methyl D-glucopyranuronate 
• 108-24-7 acetic anhydride 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 67-56-1 methanol 
• 63-29-6 D-glucurono-6,3-lactone 
• 6556-12-3 D-glucuronic acid 
• 1190935-89-7 D-glucurono-6,3-lactone 

Downstream Products

• 174264-48-3 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-{6-(tert-butyl-dimethyl-silanyloxy)-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 174264-49-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 67776-38-9 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 14365-73-2 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester 
• 1350467-71-8 methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate 
• 52173-67-8 methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 1350467-75-2 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-76-3 C₁₇H₁₅⁽²⁾H₂Cl₃O₈ 
• 1350467-77-4 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate 
• 1350467-78-5 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-79-6 methyl (phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosid)uronate 
• 1350467-81-0 phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid 
• 1350467-68-3 phenyl 4-deoxy-1-thio-α-L-threo-hex-4-enopyranosiduronic acid 
• 1350467-69-4 2,4,6-trichlorophenyl 4-deoxy-α-L-threo-hex-4-enopyranosiduronic acid 

Relevant articles and documents

Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II

A series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds 7d, 7 g, 7 h demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay.

Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles

Synthetic immune-stimulatory drugs such as agonists of the Toll-like receptors (TLR) 7/8 are potent activators of antigen-presenting cells (APCs), however, they also induce severe side effects due to leakage from the site of injection into systemic circulation. Here, we report on the design and synthesis of an amphiphilic polymer-prodrug conjugate of an imidazoquinoline TLR7/8 agonist that in aqueous medium forms vesicular structures of 200 nm. The conjugate contains an endosomal enzyme-responsive linker enabling degradation of the vesicles and release of the TLR7/8 agonist in native form after endocytosis, which results in high in vitro TLR agonist activity. In a mouse model, locally administered vesicles provoke significantly more potent and long-lasting immune stimulation in terms of interferon expression at the injection site and in draining lymphoid tissue compared to a nonamphiphilic control and the native TLR agonist. Moreover, the vesicles induce robust activation of dendritic cells in the draining lymph node in vivo.

Indole-glucoside substrate and preparation method and application thereof in detection of aerobe vaginitis (AV)

The invention discloses a glycosyl donor synthetic process, aiming to overcome defects in detection of aerobe vaginitis (AV) by the prior art. Glycosyl donor is connected with chromogen indole to generate glucosides, and an indole-glucoside substrate with good effect, high flexibility, high stability and high specificity is then synthetized. According to inspection standards, as a comparison result between the color rendering property of the synthetized substrate and that of conventional AV detection reagents, the color rendering property of the substrate is superior to that of a Chromagar AVdetection reagent. With innovation of the glycosyl donor synthetic process and the synthetic process of gluocosides by connection for synthesis of the indole-glucoside chromogenic substrate, innovation of extraction and purification and application verification, reaction yield of each stage of products is increased greatly, the products are white nearly, influence from color of the substrate to identification process is reduced, and flexibility and accuracy of AV detection are both improved greatly.

A combinatorial approach towards the synthesis of non-hydrolysable triazole-iduronic acid hybrid inhibitors of human α-l-iduronidase: Discovery of enzyme stabilizers for the potential treatment of MPSI

Preparation of substituent-diverse, triazole-iduronic acid hybrid molecules by click reaction of an azido iduronic acid derivative with randomly chosen alkynes is described. Library members were screened for their ability to inhibit α-l-iduronidase, and hit molecules and analogues were then investigated for their ability to stabilize rh-α-IDUA in a thermal denaturation study. This work resulted in the discovery of the first small molecules that can be used to stabilize exogenous rh-α-IDUA protein in vitro.

A mechanistic study of the non-oxidative decarboxylation catalyzed by the radical S-adenosyl-l-methionine enzyme BlsE involved in blasticidin S biosynthesis

Decarboxylation is a fundamentally important reaction in biology and involves highly diverse mechanisms. Here we report a mechanistic study of the non-oxidative decarboxylation catalyzed by BlsE, a radical S-adenosyl-l-methionine (SAM) enzyme involved in blasticidin S biosynthesis. Through a series of biochemical analysis with isotopically labeled reagents, we show that the BlsE-catalyzed reaction is initiated by the 5′-deoxyadenosyl (dAdo) radical-mediated hydrogen abstraction from a sugar carbon of the substrate cytosylglucuronic acid (CGA), and does not involve a carboxyl radical as has been proposed for 4-hydroxyphenylacetate decarboxylase (HPAD). Our study reveals that BlsE represents a mechanistically new type of radical-based decarboxylase.

CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self- immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

COMPOSITIONS AND METHODS RELATED TO ANTI-CD19 ANTIBODY DRUG CONJUGATES

In some aspects, the invention relates to an antibody-drug conjugate, comprising an anti-CD 19 antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self-immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

COMPOSITIONS AND METHODS RELATED TO ANTI-EGFR ANTIBODY DRUG CONJUGATES

In some aspects, the invention relates to an antibody-drug conjugate, comprising an anti-epidermal growth factor receptor ("EGFR") antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self-immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the drug; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

COMPOUNDS COMPRISING SELF-IMMOLATIVE GROUP

Provided are compounds comprising a self-immolative group, and the compounds comprising a self-immolative group according to the present invention may include a protein (for example, an oligopeptide, a polypeptide, an antibody, or the like) having substrate-specificity for a target and an active agent (for example, a drug, a toxin, a ligand, a detection probe, or the like) having a specific function or activity.