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Sigma-Aldrich

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

suitable for fluorescence, ≥99.0% (TLC)

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Synonym(s):
4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-glucopyranoside
Empirical Formula (Hill Notation):
C18H21NO8
CAS Number:
Molecular Weight:
379.36
Beilstein/REAXYS Number:
1693397
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

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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This Item
M9659M2133M6018
solubility

DMF: 20 mg/mL, clear, colorless

solubility

pyridine: 50 mg/mL, clear, colorless to faintly yellow

solubility

DMF: 20 mg/mL, clear, colorless to faintly yellow

solubility

water: 19.60-20.40 mg/mL, clear, colorless to faintly yellow

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

-

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

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)

fluorescence

-

fluorescence

-

fluorescence

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
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)
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
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.
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

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