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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Considerations in the storage of soil samples for enzyme activity analysis
Peoples MS and Koide RT
Applied soil ecology : a section of Agriculture, Ecosystems & Environment, 62(1), 98-102 (2012)
Purification and characterization of beta-N-acetylhexosaminidase I2 from human liver
Dewji NN, et al.
The Biochemical Journal, 234(1), 157-162 (1986)
beta-N-Acetylhexosaminidases HEXO1 and HEXO3 are responsible for the formation of paucimannosidic N-glycans in Arabidopsis thaliana
Liebminger E, et al.
Test, 286(12), 10793-10802 (2011)
Quantification of Chitinase Activity in Fusarium oxysporum
Ruiz-Roldan, Carmen and Roncero, M Isabel G
Bio-protocol, 6(15), 98-102 (2016)
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
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