N-azidoacetylmannosamine-tetraacylated CAS 361154-30-5

Introduction：Basic information about N-azidoacetylmannosamine-tetraacylated CAS 361154-30-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

N-azidoacetylmannosamine-tetraacylated Basic information

• Product Name: N-azidoacetylmannosamine-tetraacylated
• Synonyms: N-azidoacetylmannosamine-tetraacylated (Ac4ManNAz);N-Azidoacetylmannosamine-tetraacylated 95%;N-Azidoacetylmannosamine-tetraacylated;Ac4ManNAz,N-Azidoacetylmannosamine-tetraacylated;1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine;(3S,4R,5S,6R)-6-(Acetoxymethyl)-3-(2-azidoacetamido)tetrahydropyran-2,4,5-triyl Triacetate;2-[(2-Azidoacetyl) amino] -2-deoxy-1,3,4,6- tetra-O-acetyl-D-manno- pyranose;1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine(Ac4ManNAz)
• CAS: 361154-30-5
• MF: C16H22N4O10
• MW: 430.37
• Mol File: 361154-30-5.mol

N-azidoacetylmannosamine-tetraacylated Chemical Properties

• storage temp.: -20°C
• solubility: DMSO:100 mg/mL (232.36 mM; Need ultrasonic
• form: powder or crystals
• color: White to light yellow
• Appearance: white solid
• 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?/m1/s1
• InChIKey: HGMISDAXLUIXKM-RERKFICYNA-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|

Safety Information

• WGK Germany: WGK 3
• Storage Class: 11 - Combustible Solids

N-azidoacetylmannosamine-tetraacylated Usage And Synthesis

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.

reaction suitability

reaction type: click chemistry

storage

Store at -20°C