A fluorogenic substrate for β-hexosaminidases
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4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-Glucopyranoside

Item No. 26953

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one
CAS Number
37067-30-4
Synonyms
  • 4-Methylumbelliferyl-N-acetyl-β-Glucosaminide
  • 4-ΜU-2-acetamido-2-deoxy-β-D-Glucopyranoside
Molecular Formula
C18H21NO8
Formula Weight
379.4
Purity
≥98%
Emission
455 and 445 nm at low and high pH, respectively
Excitation
320 and 360 nm at low and high pH, respectively
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 30 mg/ml
SMILES
O=C(C)N[C@H]1[C@H](OC2=CC=C(C(C)=CC(O3)=O)C3=C2)O[C@H](CO)[C@@H](O)[C@@H]1O
InChi Code
InChI=1S/C18H21NO8/c1-8-5-14(22)26-12-6-10(3-4-11(8)12)25-18-15(19-9(2)21)17(24)16(23)13(7-20)27-18/h3-6,13,15-18,20,23-24H,7H2,1-2H3,(H,19,21)/t13-,15-,16-,17-,18-/m1/s1
InChi Key
QCTHLCFVVACBSA-JVNHZCFISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $69

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    250 mg

    $149

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    500 mg

    $248

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    1 g

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    Product Description

    4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-glucopyranoside is a fluorogenic substrate for β-hexosaminidases.1,2 Upon enzymatic cleavage by β-hexosaminidases, 4-methylumbelliferone (4-ΜU) is released and its fluorescence can be used to quantify β-hexosaminidase activity. 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high pH (7.12-10.3), respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases.3 4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-glucopyranoside has been used to quantify β-hexosaminidase activity in serum or leukocytes from patients with GM2 gangliosidoses such as Tay-Sachs disease, which is characterized by defects in the α subunit of β-hexosaminidase.2,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Leaback, D.H., and Walker, P.G. Studies on glucosaminidase. 4. The fluorimetric assay of N-acetyl-β-glucosaminidase. Biochem J. 78(1), 151-156 (1961).

    2. Wendeler, M., and Sandhoff, K. Hexosaminidase assays. Glycoconj. J. 26(8), 945-952 (2009).

    3. Zhi, H., Wang, J., Wang, S., et al. Fluorescent properties of hymecromone and fluorimetric analysis of hymecromone in compound dantong capsule. J. Spectrosc. 147128 (2013).

    4. Baek, R.C., Martin, D.R., Cox, N.R., et al. Comparative analysis of brain lipids in mice, cats, and humans with Sandhoff disease. Lipids 44(3), 197-205 (2009).