N-azidoacetylgalactosamine-tetraacylated (Ac4GaINAz) Chemical Properties

storage temp. 

-20°C

solubility 

DMSO, DMF, DCM, THF, Chloroform

form 

powder or crystals

color 

White to off-white

Appearance

white crystals

InChIKey

HGMISDAXLUIXKM-FECVBEAVNA-N

SMILES

O([C@H]1[C@H]([C@@H](COC(=O)C)OC(OC(=O)C)[C@@H]1NC(=O)CN=[N+]=[N-])OC(=O)C)C(=O)C |&1:1,2,3,15,r|

N-azidoacetylgalactosamine-tetraacylated (Ac4GaINAz) Usage And Synthesis

Description

The unnatural azido-containing monosaccharide building block. The azide moiety can be used for modification though chemoselective ligation chemistries including CuAAC, Cu-free click reaction or Staudinger ligation. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.

Uses

N-Azidoacetylgalactosamine-tetraacylated (Ac₄GalNAz) provides the first part of a simple and robust two-step technique that helps identify and characterize cell surface sialic acid-containing glycoproteins. The azide-modified protein can be detected by reaction with alkynes. For example alkynes labeled with a fluorescent probe or a biotin can be used. 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.

Application

N-Azidoacetylgalactosamine-tetraacylated (Ac4GalNAz) provides the first part of a simple and robust two-step technique that helps identify and characterize cell surface sialic acid-containing glycoproteins. The azide-modified protein can be detected by reaction with alkynes. For example alkynes labeled with a fluorescent probe or a biotin can be used. 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.

reaction suitability

reaction type: click chemistry

IC 50

Alkyl-Chain

N-azidoacetylgalactosamine-tetraacylated (Ac4GaINAz)(653600-56-7)Related Product Information

• Ac4ManNAz
• Ac4GalNAl
• Ac4GlcNAl
• 2-[(2-Azidoacetyl)amino]-2-deoxy-D-galactose
• 2-[(2-Azidoacetyl) amino] -2-deoxy-D-glu- copyranose
• 2-[(Azidoacety)amino]-2-deoxy-D-mannose
• 2-[(Azidoacetyl)aMino]-2-deoxy-D-glucose
• N–(4–pentynoyl) mannosamine tetraacylated (Ac4ManNAl)
• 2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate
• N-(4-pentynoyl)-galactosamine tetraacylated (Ac4GalNAl)
• GlcNaz
• ManNaz
• N-azidoacetylmannosamine-tetraacylated