142072-12-6

Basic information

• Product Name: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside
• Synonyms: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside;2-Azidoethyl 2-AcetaMido-2-deoxy-β-D-glucopyranoside;2-Azidoethyl 2-Acetamido-2-deoxy-β2-Azidoethyl 2-acetamido-2-deoxy-b-D-glucopyranoside
• CAS NO: 142072-12-6
• Molecular Formula: C₁₀H₁₈N₄O₆
• Molecular Weight: 290.27312
• Mol File: 142072-12-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: <0°C
• Solubility: Methanol (Slightly, Sonicated), Water (Slightly)
• CAS DataBase Reference: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside(142072-12-6)
• EPA Substance Registry System: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside(142072-12-6)

Safety Data

• Hazardous Substances Data: 142072-12-6(Hazardous Substances Data)

Usage

Description

2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside is a complex carbohydrate derivative that possesses unique structural features and functional groups. It is a modified sugar molecule with an azidoethyl group attached to the 2-acetamido-2-deoxy-beta-D-glucopyranoside backbone. This molecule is of interest in various fields due to its potential applications in chemical and biological research.

Uses

Used in Chemical Synthesis:
2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside is used as a reactant for the synthesis of various complex carbohydrates and glycoconjugates. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside is used as a reactant for the development of multipotent protein activators. These activators can potentially modulate the activity of various proteins, leading to novel therapeutic approaches for treating various diseases.
Used in Material Science:
In the field of material science, 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside can be utilized as a building block for the development of novel biomaterials. Its unique structural features and functional groups can be exploited to create materials with specific properties, such as enhanced biocompatibility or targeted drug delivery capabilities.
Used in Diagnostics:
2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside can also be employed in the development of diagnostic tools, such as glycan-based biosensors. Its unique structural features can be used to create highly specific and sensitive detection systems for various analytes, including proteins, pathogens, and other biomolecules.

InChI:InChI=1/C10H18N4O6/c1-5(16)13-7-9(18)8(17)6(4-15)20-10(7)19-3-2-12-14-11/h6-10,15,17-18H,2-4H2,1H3,(H,13,16)/t6-,7-,8+,9+,10+/m0/s1

Upstream product

• 142072-11-5 2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 85193-58-4 2-bromoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 

Downstream Products

• 724764-00-5 2-azidoethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 724763-99-9 2-azidoethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 724764-05-0 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 724764-04-9 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside 
• 186406-99-5 2-azidoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1019642-47-7 2-azidoethyl α-5-acetamido-9-(biphenylcarbonylamino)-3,5,9-trideoxy-D-glycero-2-nonulosonic acid-pyranosyl-(2->3)-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-glucopyranoside 
• 1340474-26-1 C₂₄H₃₆N₂O₁₃ 
• 64448-36-8 2-(benzyloxycarbonyl)aminoethyl 2-acetylamino-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Solid-Phase Enzymatic Synthesis of a Sialyl Lewis X Tetrasaccharide on a Sepharose Matrix

Thiopyridyl Sepharoses with different linker arm lengths were prepared from epoxy Sepharose 6B by reaction first with 1,8-diamino-3,6-dioxaoctane and then with, sucessively, diethoxy-3-cyclobutene-1,2-dione (squaric acid diethyl ester) and 1,8-diamino-3,6-dioxaoctane in several cycles, followed by reaction of the obtained amino Sepharoses with, successively, thiobutyrolactone and 2,2′-dithiopyridine. The thiopyridyl Sepharoses were reacted with the glucosamine derivative 2-(3′-mercaptobutyrylamido)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside, giving GlcNAc Sepharoses with different linker lengths. Enzymatic galactosylation of these with β-(1-4)-galactosyltransferase and UDP-galactose gave yields varying between 70 and 98%, and there was a clear correlation between linker length and yield. A GlcNAc Sepharose with a long linker was then used in a solid-phase synthesis of a sialyl Le x tetrasaccharide. The three required enzymes (galactosyl-, sialyl, and fucosyltransferase) and nucleotide sugars were reacted consecutively with the GlcNAc Sepharose, giving, after cleavage from Sepharose with DTT, the free sialyl Le x tetrasaccharide derivative in a 57% total yield after purification.

Double targeting hepatic tumor drug as well as synthetic method and application thereof

The invention relates to a double targeting hepatic tumor drug as well as a synthetic method and application thereof. The double targeting hepatic tumor drug has a terminal structure (galactose or N-acetyl galactose) capable of specifically binding to asialoglycoprotein receptor at the surface of a hepatocyte, and therefore the double targeting hepatic tumor drug is capable of binding to the asialoglycoprotein receptor so as to be brought into the interior of a hepatic tumor cell by means of the endocytosis of the hepatic tumor cell. On the other hand, experiments prove that the enzyme hydrolysis of the overexpressed cathepsin B in hepatic tumor cell lysosome is performed on the double targeting hepatic tumor drug to release Adriamycin, that is, active ingredients are released while the level of cathepsin B can be reduced, so as to slow down tumor progression. In summary, the double targeting hepatic tumor drug prepared by the invention uses asialoglycoprotein receptor and cathepsin Bas double target spots for having an effect, has obvious therapeutic effect, and meanwhile significantly reduces the toxic and side effects on other normal tissues and cells.

Photo-click immobilization on quartz crystal microbalance sensors for selective carbohydrate-protein interaction analyses

A photoclick method based on azide photoligation and Cu-catalyzed azide-alkyne cycloaddition has been evaluated for the immobilization of carbohydrates to polymeric materials. The biomolecular recognition properties of the materials have been investigated with regard to applicable polymeric substrates and selectivity of protein binding. The method was used to functionalize a range of polymeric surfaces (polystyrene, polyacrylamide, polyethylene glycol), poly(2-ethyl-2-oxazoline), and polypropene) with various carbohydrate structures (based on α-D-mannose, β-D-galactose, and N-acetyl-β-D-glucosamine). The functionalized surfaces were evaluated in real-time studies of protein-carbohydrate interactions using a quartz crystal microbalance flow-through system with a series of different carbohydrate-binding proteins (lectins). The method proved to be robust and versatile, resulting in a range of efficient sensors showing high and predictable protein selectivities.