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M2133

Sigma-Aldrich

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide

β-N-acetylhexosaminidase substrate, fluorogenic, ≥98% (TLC), powder

Synonym(s):

4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-gluco­pyrano­side

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About This Item

Empirical Formula (Hill Notation):
C18H21NO8
CAS Number:
37067-30-4
Molecular Weight:
379.36
EC Number:
253-333-0
UNSPSC Code:
12352204
PubChem Substance ID:
24896605
NACRES:
NA.32

Product Name

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide, β-N-acetylhexosaminidase substrate

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

DMF: 20 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1Oc2ccc3C(C)=CC(=O)Oc3c2

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-XWEABGILSA-N

General description

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide (4-MUF-NAG) contains chitin monomer, N-acetyl-D-glucosamine (NAG) and a 4-methylumbelliferone (7-hydroxy-4-methylcoumarin) (4-MUF) moiety.

Application

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide has been used as a substrate for assaying
  • β-N-acetylglucosaminidase (NAGase) from soil samples
  • chitinase from Fusarium oxysporum using fluorimetric assay
  • β-N-acetylhexosaminidases from Arabidopsis thaliana roots and leaves samples

Biochem/physiol Actions

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide (4-MUF-NAG) is a synthetic fluorogenic substrate for N-acetyl-β-D-glucosaminidase (NAGase). The enzyme functionality is assessed by its ability to hydrolyze the N-acetyl-D-glucosamine (NAG) residue in 4-MUF-NAG. 4-MUF-NAG is also a substrate for Chitinase and N-acetylhexosaminidase.

Substrates

Fluorogenic substrate for β-N-acetylhexosaminidase

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000423223
0000423221
0000423223
0000423221
0000417804

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Li Ou et al.
Gene therapy, 27(5), 226-236 (2020-01-04)
The GM2-gangliosidoses are neurological diseases causing premature death, thus developing effective treatment protocols is urgent. GM2-gangliosidoses result from deficiency of a lysosomal enzyme β-hexosaminidase (Hex) and subsequent accumulation of GM2 gangliosides. Genetic changes in HEXA, encoding the Hex α subunit
4-MUF-NAG for fungal biomass determination: Scope and limitations in the context of biodeteriorationstudies
Sequeira S, et al.
Journal of cultural heritage, 22, 992-998 (2016)
Christian Hinderer et al.
Human gene therapy, 31(21-22), 1169-1177 (2020-10-14)
GM1 gangliosidosis is a rare neurodegenerative lysosomal storage disease caused by loss-of-function mutations in the gene encoding beta-galactosidase (β-gal). There are no approved treatments for GM1 gangliosidosis. Previous studies in animal models have demonstrated that adeno-associated viral (AAV) vector-mediated gene
Quantification of Chitinase Activity in Fusarium oxysporum
Ruiz-Roldan, Carmen and Roncero, M Isabel G
Bio-protocol, 6(15), 98-102 (2016)
M O'Brien et al.
Applied and environmental microbiology, 53(7), 1718-1720 (1987-07-01)
A total of 101 strains of bacteria from environmental and clinical sources, most of which were gram negative, were tested for chitobiase activity by using a filter paper spot test with 4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide as the substrate. The results were compared with
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