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ChemicalBook--->CAS DataBase List--->361154-30-5

361154-30-5

361154-30-5 Structure

361154-30-5 Structure
IdentificationBack Directory
[Name]

N-azidoacetylmannosamine-tetraacylated (Ac4ManNAz)
[CAS]

361154-30-5
[Synonyms]

N-Azidoacetylmannosamine-tetraacylated
N-Azidoacetylmannosamine-tetraacylated 95%
1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine
Ac4ManNAz,N-Azidoacetylmannosamine-tetraacylated
N-azidoacetylmannosamine-tetraacylated (Ac4ManNAz)
1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine(Ac4ManNAz)
2-[(2-Azidoacetyl) amino] -2-deoxy-1,3,4,6- tetra-O-acetyl-D-manno- pyranose
(3S,4R,5S,6R)-6-(Acetoxymethyl)-3-(2-azidoacetamido)tetrahydropyran-2,4,5-triyl Triacetate
(3S,4R,5S,6R)-6-(acetoxymethyl)-3-(2-azidoacetamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate
[Molecular Formula]

C16H22N4O10
[MDL Number]

MFCD26961126
[MOL File]

361154-30-5.mol
[Molecular Weight]

430.37
Chemical PropertiesBack Directory
[storage temp. ]

-20°C
[solubility ]

DMSO:100 mg/mL (232.36 mM; Need ultrasonic
[form ]

powder or crystals
[color ]

White to light yellow
Hazard InformationBack Directory
[Application]

N-Azidoacetylmannosamine-tetraacylated (Ac4ManNAz) is an azide-containing metabolic glycoprotein labeling reagent that can be incorporated into the sialic acid biosynthesis pathway. 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.
[Description]

N-azidoacetylmannosamine-tetraacylated (Ac4ManNAz) is an 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]

Tetraacylated N-azidoacetylmannosamine is generally used in click chemistry applications in bioconjugate chemistry.
[storage]

Store at -20°C
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