98924-81-3
Chemical Structure
Ac4GlcNAz
Synonym(s): N-azidoacetylglucosamine-tetraacylated
- CAS No.: 98924-81-3
- Formula:C16H22N4O10
- Molecular Weight:430.37
IUPAC Name: (3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-azidoacetamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate
InChIKey: HGMISDAXLUIXKM-ALTVCHKUSA-N
SMILES: CC(O[C@@H]1[C@H](C(O[C@@H]([C@H]1OC(C)=O)COC(C)=O)OC(C)=O)NC(CN=[N+]=[N-])=O)=O
Biological Activity: Ac4GlcNAz (N-azidoacetylglucosamine-tetraacylated) is an azido-containing fully acetylated N-acetylglucosamine analog, a metabolic glycan marker, and also an inducer of S-glycosylation. Ac4GlcNAz can be taken up by bacteria, processed via endogenous carbohydrate biosynthesis pathways, and integrated into glycans by replacing natural monosaccharides. Under alkali promotion, Ac4GlcNAz undergoes β-elimination to form α,β-unsaturated aldehydes, which then bind to cysteine residues via Michael addition. Ac4GlcNAz can be integrated into glycoproteins. Ac4GlcNAz is applicable to research related to Helicobacter pylori infection[1][2].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Ac4GlcNAz | 99.49% | Ac4GlcNAz (N-azidoacetylglucosamine-tetraacylated) is an azido-containing fully acetylated N-acetylglucosamine analog, a metabolic glycan marker, and also an inducer of S-glycosylation. Ac4GlcNAz can be taken up by bacteria, processed via endogenous carbohydrate biosynthesis pathways, and integrated into glycans by replacing natural monosaccharides. Under alkali promotion, Ac4GlcNAz undergoes β-elimination to form α,β-unsaturated aldehydes, which then bind to cysteine residues via Michael addition. Ac4GlcNAz can be integrated into glycoproteins. Ac4GlcNAz is applicable to research related to Helicobacter pylori infection. | ||||||||||||||||||||
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Similarity Score 1.00
HY-118297Ac4ManNAz (80% α isomer) -
Similarity Score 1.00
HY-141128Ac4GalNAz -
Similarity Score 1.00
HY-W728531Ac4ManNAz -
Similarity Score 0.84
HY-114998α-D-Glucosamine pentaacetate -
Similarity Score 0.84
HY-117271D-Galactosamine pentaacetate -
Similarity Score 0.84
HY-W005729β-D-Galactosamine pentaacetate -
Similarity Score 0.84
HY-W009020β-D-Glucopyranose,2-(acetylamino)-2-deoxy,1,3,4,6-tetraacetate -
Similarity Score 0.84
HY-W1279002-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose -
Similarity Score 0.84
HY-W613261α-D-Galactopyranose,2-(acetylamino)-2-deoxy-,1,3,4,6-tetraacetate -
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References
- [1]. Luong P, et al. Synthesis and Application of Rare Deoxy Amino l-Sugar Analogues to Probe Glycans in Pathogenic Bacteria. ACS infectious diseases. 2022 Apr 08;8(4):889-900. [Content Brief]
- [2]. Clark EL, et al. Development of Rare Bacterial Monosaccharide Analogs for Metabolic Glycan Labeling in Pathogenic Bacteria. ACS chemical biology. 2016 Dec 16;11(12):3365-3373. [Content Brief]
