2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate

Base Information

• Chemical Name: 2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate
• CAS No.: 98924-81-3
• Molecular Formula: C₁₆H₂₂N₄O₁₀
• Molecular Weight: 430.371
• Mol file: 98924-81-3.mol

Synonyms:2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate;1,3,4,6-Tetra-O-acetyl-2-(2-azidoacetamido)-2-deoxy-b-D-glucopyranose

Chemical Property of 2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate

Chemical Property:

• PSA: 196.77000
• LogP: -0.21094
• Storage Temp.: -20°C

Purity/Quality:

N-Azidoacetylglucosamine,Acetylated ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,3,4,6-Tetra-O-acetyl-N-azidoacetylglucosamine is an important organic building block to synthetize substituted glucosamine products. N-Azidoacetylglucosamine is a metabolic glycoprotein labeling reagent that is introduced metabolically in model organisms. The reactive azide group in N-Azidoacetylglucosamine will react with phosphines for visualization or selective capture. N-azidoacetylglucosamine-tetraacylated (Ac4GlcNAz) provides the first part of a simple and robust two-step technique that helps identify and characterize cell surface sialic acid-containing glycoproteins. The acetyl groups increase cell permeability and allow the unnatural sugars to easily pass through the cell membrane. Carboxyesterases remove the acetyl groups once the monosaccharide is in the cell. The azide-modified protein is detected with either fluorescent alkynes or biotin alkyne.
• Description: N-azidoacetylglucosamine-tetraacylated (Ac4GlcNAz) is an azido-tagged analogue of N-acetylglucosamine (GlcNAC). It features azide functionality on the N-acyl side chain and is acetylated to aid in cell membrane permeation. Once in the cell, the acetylated compound is deprotected and takes part in the hexosamine biosynthetic pathway by action of GlcNAc kinase. The resulting modified proteins are detected by the addition of fluorescent tags under Cu(I)-catalyzed azide-alkyne cycloaddition conditions.

Technology Process of 2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate

There total 26 articles about 2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

acetic anhydride (108-24-7) + 2-(azidoacetamido)-2-deoxy-D-mannopyranose → 1,3,4,6-tetra-O-acetyl-2-azidoacetylamido-2-deoxy-α,β-D-mannopyranose (653600-56-7,98924-81-3,1404472-50-9)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; for 10h;

DOI:10.1021/ja027748x

Reference yield: 91.0%

1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside (68499-56-9) → 1,3,4,6-tetra-O-acetyl-2-azidoacetamide-2-deoxy-β-D-glucopyranose (857677-98-6,653600-56-7,98924-81-3,1404472-50-9)

Guidance literature:

With sodium azide;

DOI:10.1080/10426507.2017.1311332

Reference yield: 84.0%

N-azidoacetylgalactosamine + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-azidoacetylamino-D-galactopyranose (653600-56-7,98924-81-3,1404472-50-9)

Guidance literature:

With pyridine;

DOI:10.1021/ja104547x

upstream raw materials:

2-azidoacetyl chloride

tetra-acetyl glucosamine

1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose

Refernces

• 1、 Chinoy, Zoeisha S.,Bodineau, Clément,Favre, Camille,Moremen, Kelley W.,Durán, Raúl V.,Friscourt, Frédéric. "Selective Engineering of Linkage-Specific α2,6-N-Linked Sialoproteins Using Sydnone-Modified Sialic Acid Bioorthogonal Reporters". supporting information. p. 4281 - 4285. Retrieved 2019/02/28.
• 2、 Shen, Li,Cai, Kaimin,Yu, Jin,Cheng, Jianjun. "Novel Liposomal Azido Mannosamine Lipids on Metabolic Cell Labeling and Imaging via Cu-Free Click Chemistry". . p. 2317 - 2322. Retrieved 2019/09/06.