A ManNAc analog and building block
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1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α-D-Mannopyranose

Item No. 30542

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-azido-2-deoxy-α-D-mannopyranose, 1,3,4,6-tetraacetate
CAS Number
68733-20-0
Molecular Formula
C14H19N3O9
Formula Weight
373.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:3): 0.25 mg/mlDMSO: 15 mg/ml
SMILES
O=C(C)O[C@@H]1[C@@H](N=[N+]=[N-])[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1
InChi Code
InChI=1S/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11+,12-,13-,14+/m1/s1
InChi Key
QKGHBQJLEHAMKJ-ITGHMWBKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose is an analog of N-acetylmannosamine (ManNAc) and a building block.1,2 It has been used as a precursor in the synthesis of differently substituted trimers of the group A N. meningitidis capsular polysaccharide repeating unit for use in immunological experiments.2 It has also been used in the synthesis of fluorescent probes for lysosomal labeling.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Saxon, E., Luchansky, S.J., Hang, H.C., et al. Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation. J. Am. Chem. Soc. 124(50), 14893-14902 (2002).

    2. Slättegård, R., Teodorovic, P., Kinfe, H.H., et al. Synthesis of structures corresponding to the capsular polysaccharide of Neisseria meningitidis group A. Org. Biomol. Chem. 3(20), 3782-3787 (2005).

    3. Yapici, N.B., Bi, Y., Li, P., et al. Highly stable and sensitive fluorescent probes (LysoProbes) for lysosomal labeling and tracking. Sci. Rep. 5, 8576 (2015).