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

Name: 2′-(4-Methylumbelliferyl)-α-<SC>D</SC>-<I>N</I>-acetylneuraminic acid sodium salt hydrate
Brand: SIGMA

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

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

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₄NNaO₁₁ · xH₂O

CAS Number:

76204-02-9

Molecular Weight:

489.41 (anhydrous basis)

UNSPSC Code:

12352106

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

λ_ex 315 nm; λ_em 374 nm (pH.7.0)
λ_ex 365 nm; λ_em 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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Detection Substrates & Enzymes

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.

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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Synthesis of novel N-acetylneuraminic acid derivatives as substrates for rapid detection of influenza virus neuraminidase.

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

The quenching effect of flavonoids on 4-methylumbelliferone, a potential pitfall in fluorimetric neuraminidase inhibition assays.

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

A microplate-based screening assay for neuraminidase inhibitors.

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

Role of Sialic Acid in Brachyspira hyodysenteriae Adhesion to Pig Colonic Mucins.

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

Structure-guided discovery of potent and dual-acting human parainfluenza virus haemagglutinin-neuraminidase inhibitors.

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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