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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:
Molecular Weight:
379.36
Beilstein:
1693397
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

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

Quality Level

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.

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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Nick Konkol et al.
Journal of microbiological methods, 80(2), 178-182 (2009-12-23)
A wide variety of cultural heritage materials are susceptible to fungal deterioration. The paper, canvas, and stone constituents of our cultural heritage are subjected to harmful physical and chemical processes as they are slowly consumed by fungi. Remediation of fungal
Population and biomarker responses of Daphnia magna towards anticholinesterase exposures
Lang Q and Li S
Cogent Biology, 5, 1616363-1616363 (2019)
R M Clegg et al.
Biochemistry, 22(20), 4797-4804 (1983-09-27)
Temperature-jump relaxation methods have been used to study the binding kinetics of fluorescent 4-methylumbelliferyl glycosides of N-acetyl-beta-D-glucosamine and its beta (1 leads to 4)-linked di- and trisaccharides with wheat germ agglutinin. The mono- and disaccharide derivatives yielded biexponential progress curves.
W He et al.
Prenatal diagnosis, 14(1), 17-22 (1994-01-01)
A new fluorogenic substrate, 4-methylumbelliferyl beta-D-glucosaminide, was used for the assay of acetyl CoA:glucosaminide N-acetyltransferase in chorionic villi, cultured villus cells, and amniocytes. Optimal conditions for the assay and the ranges of enzyme activity were established for the various types
Ontogeny and diurnal patterns of molecular gene expression and activity of digestive enzymes in developing greater amberjack
Gamberoni P, et al.
Aquaculture (Amsterdam, Netherlands), 534, 736330-736330 (2021)

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