N-Azidoacetylmannosamine-tetraacylated（Ac4ManNAz） - ≥98%, α and β isomer mixture , CAS No.361154-30-5

CAS: 361154-30-5 Cat. No.: T303546 Molecular Weight: 430.37

GRADE & PURITY ≥98%, α and β isomer mixture

Synonyms

Ac4ManNAz | 1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

Synonyms

Ac4ManNAz | 1, 3, 4, 6-Tetra-O-acetyl-N-azidoacetylmannosamine

Specifications & Purity

≥98%, α and β isomer mixture

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488202227
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488202227
• Canonical Smiles: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)NC(=O)CN=[N+]=[N-])OC(=O)C)OC(=O)C
• IUPAC Name: [(2R,3S,4R,5S)-3,4,6-triacetyloxy-5-[(2-azidoacetyl)amino]oxan-2-yl]methyl acetate
• InChIKey: HGMISDAXLUIXKM-LIADDWGISA-N
• 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
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H](C(O1)OC(=O)C)NC(=O)CN=[N+]=[N-])OC(=O)C)OC(=O)C
• Alternate CAS: 1094268-54-8
• Molecular Weight: 430.37
• Reaxy-Rn: 40991084
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=40991084&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 N-acyl-alpha-hexosamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: N-acyl-alpha-hexosamines
• Alternative Parents: Tetracarboxylic acids and derivatives Alpha amino acids and derivatives Oxanes Monosaccharides Secondary carboxylic acid amides Carboxylic acid esters Azo imides Azo compounds Oxacyclic compounds Acetals Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: N-acyl-alpha-hexosamine - Tetracarboxylic acid or derivatives - Alpha-amino acid or derivatives - Oxane - Monosaccharide - Secondary carboxylic acid amide - Carboxylic acid ester - Carboxamide group - Azo imide - Azo compound - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Acetal - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic zwitterion - Organonitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Air sensitive ；Heat sensitive
• Molecular Weight: 430.370 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 12
• Exact Mass: 430.134 Da
• Monoisotopic Mass: 430.134 Da
• Topological Polar Surface Area: 158.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 736.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zichun Li, Yifan Liu, Feiran Liu, Guochen Sun, Xiaoling Zhang, Jing Jing.  (2025)  Bioorthogonal click chemistry and aptamer-targeting enables highly selective fluorescence labeling of exosomal glycosylated EpCAM for super resolved imaging.  ANALYTICA CHIMICA ACTA,      [PMID:39832878] [10.1016/j.aca.2025.343623]

2. Yueping Li, Shanshan Shan, Ruru Zhang, Chaoping Sun, Xuelan Hu, Jiada Fan, Yi Wang, Ruixue Duan, Mingyuan Gao.  (2024)  Imaging and Downstaging Bladder Cancer with the 177Lu-Labeled Bioorthogonal Nanoprobe.  ACS Nano,      [PMID:38904444] [10.1021/acsnano.4c04303]

3. Gongxi Qiao, Shenglin Li, Xumin Pan, Ping Xie, Ruixi Peng, Xiangrong Huang, Mengyun He, Jianhui Jiang, Xia Chu.  (2024)  Surgical tumor–derived nanoplatform targets tumor-associated macrophage for personalized postsurgical cancer immunotherapy.  Science Advances,  10  (13):   [PMID:38536926] [10.1126/sciadv.adk7955]

4. Ren Tingju, Zhang Yingzhi, Tong Yuxiao, Zhang Qi, Wang Tianhao, Wang Yue, Yang Chunguang, Xu Zhangrun.  (2025)  FRET imaging of glycoRNA on small extracellular vesicles enabling sensitive cancer diagnostics.  Nature Communications,  16  (1): (1-19).  [PMID:40210865] [10.1038/s41467-025-58490-2]

5. Buwei Hu, Hui Wang, Chenli Ji, Xuehan Xu, Luyi Wang, Tingting Cao, Menghua Gao, Yanjun Zhao, Bin Wang, Wenjing Xuan, Jianjun Cheng.  (2026)  Enhanced Corneal Retention of Hyaluronic Acid via Metabolic Glycoengineering-based In Vivo Bioorthogonal Reaction.  Biomaterials Science,      [PMID:] [10.1039/D5BM01898F]