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69585

Sigma-Aldrich

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

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

Synonyme(s) :

4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-glucopyranoside

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About This Item

Formule empirique (notation de Hill) :
C18H21NO8
Numéro CAS:
Poids moléculaire :
379.36
Beilstein:
1693397
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352204
ID de substance PubChem :
Nomenclature NACRES :
NA.32

Nom du produit

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

Essai

≥99.0% (TLC)

Forme

powder

Impuretés

≤0.1% free 4-methylumbelliferone

Solubilité

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)

Adéquation

suitable for fluorescence

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Autres remarques

Assay of β-N-acetylhexosaminidase

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

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.
C Emiliani et al.
The International journal of biochemistry, 23(2), 215-219 (1991-01-01)
1. Rat liver beta-N-acetylhexosaminidase was separated into several different molecular forms by DEAE-cellulose chromatography. 2. The subunit composition of the isoenzymes, as well as the similarities to human hexosaminidases, were determined by using the specific active alpha subunit substrate 4-methylumbelliferyl-beta-N-acetylglucosamine-6-sulphate.
C T Yuen et al.
Annals of clinical biochemistry, 21 ( Pt 4), 295-300 (1984-07-01)
This paper describes a comparison of the recently developed substrate 2-methoxy-4-(2'-nitrovinyl)-phenyl-2-acetamido-2-deoxy-beta-D-gluc opyranoside (MNP-GlcNAc) and the corresponding 4-methylumbelliferyl substrate (4-MU-GlcNAc) for the determination of urinary NAG. A good correlation (r = 0.977) was found between NAG activities in 366 urine samples
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
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

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