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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

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

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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Purification and characterization of beta-N-acetylhexosaminidase I2 from human liver
Dewji NN, et al.
The Biochemical Journal, 234(1), 157-162 (1986)
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)
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)
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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