A fluorogenic substrate of neuraminidases
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4-Methylumbelliferyl-N-acetyl-α-D-Neuraminic Acid (sodium salt)

Item No. 16620

Technical Information
Formal Name
4-methyl-2-oxo-2H-1-benzopyran-7-yl 5-(acetylamino)-3,5-dideoxy-α-neuraminic acid, monosodium salt
CAS Number
76204-02-9
Synonyms
  • 4-MUNANA
  • Neu5Ac-α-4MU
  • Sodium 2-(4-methylumbelliferyl)-N-acetylneuraminate
Molecular Formula
C21H24NO11 • Na
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 15 mg/mlDMSO: 20 mg/mlEthanol: 0.25 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
317 nm
SMILES
O=C1C=C(C)C2=CC=C(O[C@]3(C([O-])=O)C[C@H](O)[C@@H](NC(C)=O)[C@@]([C@H](O)[C@H](O)CO)([H])O3)C=C2O1.[Na+]
InChi Code
InChI=1S/C21H25NO11.Na/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23;/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30);/q;+1/p-1/t13-,14+,17+,18+,19+,21+;/m0./s1
InChi Key
NNNXBDLJYKMDAI-NLSRWXBQSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid is a fluorogenic substrate of neuraminidases.1 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid is cleaved by neuraminidases to release the fluorescence moiety 4-methylumbelliferyl (4-MU). 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high (7.12-10.3) pH, respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases. 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid has been used to quantify neuraminidase activity in mammalian cells and clinical isolates of influenza virus.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Monti, E., Preti, A., Nesti, C., et alExpression of a novel human sialidase encoded by the NEU2 gene. Glycobiology 9(12), 1313-1321 (1999).

    2. Stamatos, N.M., Liang, F., Nan, X., et alDifferential expression of endogenous sialidases of human monocytes during cellular differentiation into macrophages. FEBS J. 272(10), 2545-2556 (2005).

    3. Cross, A.S., Hyun, S.W., Miranda-Ribera, A., et alNEU1 and NEU3 sialidase activity expressed in human lung microvascular endothelia: NEU1 restrains endothelial cell migration, whereas NEU3 does not. The Journal of Biological Chemisty 287(19), 15966-15980 (2012).

    4. Wetherall, N.T., Trivedi, T., Zeller, J., et alEvaluation of neuraminidase enzyme assays using different substrates to measure susceptibility of influenza virus clinical isolates to neuraminidase inhibitors: Report of the neuraminidase inhibitor susceptibility network. J. Clin. Microbiol. 41(2), 742-750 (2003).