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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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K S Chen et al.
Electrophoresis, 15(5), 662-665 (1994-05-01)
A method for the detection of N-acetylglucosaminidase (GlcNAcase) activity has been developed by using 4-methyl-umbelliferyl-N-acetyl-D-glucosaminide (4-MU-GlcNAc) as substrate in crossed immunoelectrophoresis (CIE) and sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) gels. Visualization of the reaction with a 366 nm ultra-violet light
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)
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
Xiaoxiong Zeng et al.
Biotechnology letters, 27(19), 1461-1465 (2005-10-19)
4-Methylumbelliferyl N-acetyllactosaminide and 4-methylumbelliferyl sialyl N-acetyllactosaminides, which are used for the assay of sialytransferase, neuraminidase and fucosyltransferase, were synthesized, respectively, by the beta-D: -galactosidase from Bacillus circulans and by a recombinant rat alpha2,3-(N)-sialyltransferase or rat liver alpha2,6-(N)-sialyltransferase with CMP-N-acetylneuraminic acid
M G Ribeiro et al.
Journal of inherited metabolic disease, 14(5), 715-720 (1991-01-01)
GM2-gangliosidosis B1 variant is thought to be a rare disorder with a wide geographical and ethnic distribution. We report the biochemical findings obtained in different specimens from a group of 11 B1 variant patients originating from the north of Portugal.
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