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69587

Sigma-Aldrich

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate

suitable for fluorescence, BioReagent, ≥96.5% (HPLC)

All Photos(1)
Synonym(s):
4-MUNANA, 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid sodium salt hydrate, 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid sodium salt hydrate
Empirical Formula (Hill Notation):
C21H24NNaO11 · xH2O
CAS Number:
76204-02-9
Molecular Weight:
489.41 (anhydrous basis)
NACRES:
NA.32

product line

BioReagent

Assay

≥96.5% (HPLC)

form

powder

impurities

≤0.5% free 4-methylumbelliferone
≤10% water

solubility

H2O: 50 mg/mL, clear, very slightly yellow

fluorescence

λex 315 nm; λem 374 nm (pH.7.0)
λex 365 nm; λem 445 nm (after cleavage by neuraminidase)

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

O.[H]C(O)(CO)[C@]([H])(O)[C@@H]1OC(C[C@H](O)[C@H]1NC(C)=O)(Oc2ccc3C(C)=CC(=O)Oc3c2)C(=O)O[Na]

InChI

1S/C21H25NO11.Na.H2O/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23;;/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30);;1H2/q;+1;/p-1/t13-,14?,17+,18?,19+,21+;;/m0../s1

InChI key

NSQMRVBWXQQIKF-NVRWCLOTSA-M

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This Item
M8639G588908450
2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate suitable for fluorescence, BioReagent, ≥96.5% (HPLC)

Sigma-Aldrich

69587

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate ≥95% (HPLC)

Sigma-Aldrich

M8639

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate

L-Glutamic acid monosodium salt hydrate BioReagent, suitable for cell culture, suitable for insect cell culture, ≥99%

Sigma-Aldrich

G5889

L-Glutamic acid monosodium salt hydrate

7-Amino-4-methyl-3-coumarinacetic acid N-succinimidyl ester BioReagent, suitable for fluorescence, ≥90% (HPLC)

Sigma-Aldrich

08450

7-Amino-4-methyl-3-coumarinacetic acid N-succinimidyl ester

form

powder

form

powder

form

powder

form

-

solubility

H2O: 50 mg/mL, clear, very slightly yellow

solubility

water: 50 mg/mL, clear to slightly hazy, colorless to light yellow

solubility

-

solubility

DMF: soluble, DMSO: soluble

fluorescence

λex 315 nm; λem 374 nm (pH.7.0), λex 365 nm; λem 445 nm (after cleavage by neuraminidase)

fluorescence

-

fluorescence

-

fluorescence

λex 354 nm; λem 440 nm in methanol

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

suitable for fluorescence

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

General description

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid or 4-MUNANA is a synthetic fluorometric substrate that mimics the naturally occurring neuraminidase enzyme substrate. The enzyme-substrate hydrolysis results in the product 4-methylumbelliferone (4-MU), measured fluorometrically.

Application

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid or 4-MUNANA is used as a substrate for the development of a microplate-based assay for neuraminidase inhibitors. The fluorogenic substrate 2ʹ-(4-methylumbelliferyl)-α-D-N-acetylneuraminic acid (4-MUNANA) is used to study the molecular mechanisms of aspirin and celecoxib targeting mammalian neuraminidase-1.

Biochem/physiol Actions

Substrate for fluorometric assay of neuraminidase. Used for fluorescent staining of sialidases in PAGE.

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

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Wei Yang et al.
Carbohydrate research, 359, 92-96 (2012-08-29)
Two novel N-acetylneuraminic acid derivatives, luciferyl N-acetylneuraminic acid (1) and luciferyl 4,7-di-O-methyl-N-acetylneuraminic acid (2), were designed and synthesized as substrates for the rapid detection of influenza virus neuraminidase. The sensitivity and specificity of the assays with compound 1 or 2
A F Li et al.
Drug discoveries & therapeutics, 3(6), 260-265 (2009-12-01)
Neuraminidase (NA) represents a highly promising new target for drug development in influenza virus genes. Rapid screening of enzyme inhibitors is a key method for the identification of leading compounds. In order to speed up the screening for enzyme inhibitors
Jarinrat Kongkamnerd et al.
Journal of biomolecular screening, 16(7), 755-764 (2011-06-04)
Many assays aimed to test the inhibitory effects of synthetic molecules, and naturally occurring products on the neuraminidase activity exploit the hydrolysis of 2'-O-(4-methylumbelliferyl)-N-acetylneuraminic acid (4-MUNANA). The amount of the released product, 4-methylumbelliferone (4-MU), is then measured fluorimetrically. The authors
Macarena P Quintana-Hayashi et al.
Infection and immunity, 87(7) (2019-04-17)
Infection with Brachyspira hyodysenteriae results in mucoid hemorrhagic diarrhea. This pathogen is associated with the colonic mucus layer, mainly composed of mucins. Infection regulates mucin O-glycosylation in the colon and increases mucin secretion as well as B. hyodysenteriae binding sites
Patrice Guillon et al.
Nature communications, 5, 5268-5268 (2014-10-21)
Human parainfluenza viruses (hPIVs) cause upper and lower respiratory tract disease in children that results in a significant number of hospitalizations and impacts health systems worldwide. To date, neither antiviral drugs nor vaccines are approved for clinical use against parainfluenza
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