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M2133

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

Name: 4-Methylumbelliferyl N-acetyl-β-<SC>D</SC>-glucosaminide
Brand: SIGMA

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

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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Quantification of Chitinase Activity in Fusarium oxysporum

Ruiz-Roldan, Carmen and Roncero, M Isabel G

Bio-protocol, 6(15), 98-102 (2016)

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)

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)

A novel gene editing system to treat both Tay-Sachs and Sandhoff diseases.

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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