| Identification | Back Directory | [Name]
N-azidoacetylgalactosamine-tetraacylated (Ac4GaINAz) | [CAS]
653600-56-7 | [Synonyms]
Ac4GalNAz
N-Azidoacetylgalactosamine, Acylated
N-Azidoacetylgalactosamine-tetraacylated
1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine
N-azidoacetylgalactosamine-tetraacylated (Ac4GaINAz)
N-N-azidoacetylgalactosamine-tetraacylated (Ac4GalNAz)
N-azidoacetylgalactosamine-tetraacylated (Ac4GaINAz) USP/EP/BP
1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranos
2-[(2-Azidoacetyl) amino] -2-deoxy-1,3,4,6- tetra-O-acetyl-D-galac- topyranose | [Molecular Formula]
C16H22N4O10 | [MDL Number]
MFCD26961128 | [MOL File]
653600-56-7.mol | [Molecular Weight]
430.37 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMSO, DMF, DCM, THF, Chloroform | [form ]
powder or crystals | [color ]
White to off-white | [Appearance]
white crystals | [InChI]
1S/C16H22N4O10/c1-7(21)26-6-11-14(27-8(2)22)15(28-9(3)23)13(16(30-11)29-10(4)24)19-12(25)5-18-20-17/h11,13-16H,5-6H2,1-4H3,(H,19,25)/t11?,13?,14-,15?,16+/m0/s1 | [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| |
| Hazard Information | Back Directory | [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 |
|
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Sigma-Aldrich
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