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69585

Sigma-Aldrich

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

fluorogenic, ≥99.0% (TLC), powder, suitable for fluorescence

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
Beilstein:
1693397
EC Number:
253-333-0
MDL number:
MFCD00150977
UNSPSC Code:
12352204
PubChem Substance ID:
57652199
NACRES:
NA.32

product name

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide, suitable for fluorescence, ≥99.0% (TLC)

Assay

≥99.0% (TLC)

form

powder

impurities

≤0.1% free 4-methylumbelliferone

solubility

DMF: 20 mg/mL, clear, colorless

fluorescence

λex 317 nm (pH 10.0)
λex 365 nm; λem 445 nm in aqueous buffer pH 5.0 (after cleavage by β-N-acetylglucosaminidase)

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

[H]O[H].[H]O[H].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/C18H21NO8.2H2O/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);2*1H2/t13-,15-,16-,17-,18-;;/m1../s1

InChI key

PAVCYMSNMRWMAK-DMYIEBNJSA-N

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Application

4-Methylumbelliferyl N-acetyl-β-D-glucosaminide has been used as a fluorogenic substrate in the acidic chitinase activity assay. It has also been used to measure the total activity of β-N-acetylhexosaminidase (NAGase) in water sample filtrates.

Biochem/physiol Actions

4-Methylumbelliferyl-N-acetyl-β-D-glucosaminide (4-MUF-NAG) is a synthetic uncharged fluorogenic substrate for hexosaminidases. It consists of chitin monomer (N-acetyl-β-D-glucosaminide) and 4-methylumbelliferone (7-hydroxy-4-methylcoumarin) (4-MUF). 4-MUF-NAG is used for the detection and estimation of fungal growth by measuring the β-N-acetylhexosaminidase (NAGase) activity.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
Assay of 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)

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Ingunn A Hoell et al.
Biochimica et biophysica acta, 1748(2), 180-190 (2005-03-17)
We describe the overexpression and characterization of a new 30 kDa family 18 chitinase (Ech30) from Trichoderma atroviride strain P1. Sequence alignments indicate that the active site architecture of Ech30 resembles that of endochitinases such as hevamine from the rubber
Michaela Wendeler et al.
Glycoconjugate journal, 26(8), 945-952 (2008-05-14)
beta-Hexosaminidases (EC 3.2.1.52) are lysosomal enzymes that remove terminal beta-glycosidically bound N-acetylglucosamine and N-acetylgalactosamine residues from a number of glycoconjugates. Reliable assay systems are particularly important for the diagnosis of a family of lysosomal storage disorders, the GM2 gangliosidoses that
E C Landels et al.
Journal of medical genetics, 28(2), 101-109 (1991-02-01)
An assay for measuring hexosaminidase A in serum and leucocytes is described in which a centrifugal analyser is used for automation of the enzyme assays after manual heat inactivation. The assay was used in a screening programme to identify heterozygotes
J Charrow et al.
Clinical genetics, 27(1), 78-84 (1985-01-01)
A non-Jewish child with late onset GM2 gangliosidosis is described. Tissues from the patient had near normal hexosaminidase A (hex A) activity using 4-methylumbelliferyl-2-acetamido-2-deoxy-beta-D-glucopyranoside (MU-glcNAc) as substrate, and deficient activity when assayed with the 6-sulphate derivative of MU-glcNAc (MU-glcNAcS) or
B el Moudni et al.
Experimental parasitology, 83(2), 167-173 (1996-07-01)
N-Acetyl-beta-D-glucosaminidase activity was recovered in cell-free extracts of Trypanosoma cruzi epimastigotes. This enzyme was identified on the basis of its ability to hydrolyze the fluorogenic substrate 4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide. This activity was purified to apparent homogeneity by anion exchange and molecular sieve
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