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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

BioReagent, suitable for fluorescence, ≥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)

MDL number:

MFCD00057309

UNSPSC Code:

12352106

NACRES:

NA.32

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Properties

product line

BioReagent

assay

≥96.5% (HPLC)

form

powder

mol wt

489.41 g/mol (anhydrous basis)

composition

free 4-methylumbelliferone, ≤0.5% , water, ≤10%

impurities

≤0.5% free 4-methylumbelliferone, ≤10% water

color

white to faint yellow

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

Description

General description

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid or 4-MUNANA is a synthetic fluorometric substrate[1] that mimics the naturally occurring neuraminidase enzyme substrate.[2] The enzyme-substrate hydrolysis results in the product 4-methylumbelliferone (4-MU), measured fluorometrically.[2]

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.[3] 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.[4]

Biochem/physiol Actions

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

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This Item	M8639	69602	69591
Sigma-Aldrich 69587 2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate	Sigma-Aldrich M8639 2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate	Sigma-Aldrich 69602 4-Methylumbelliferyl-β-D-glucuronide hydrate	Sigma-Aldrich 69591 4-Methylumbelliferyl α-D-glucopyranoside
assay ≥96.5% (HPLC)	assay ≥95% (HPLC)	assay ≥99.0% (HPLC)	assay ≥98% (TLC)
solubility H₂O: 50 mg/mL, clear, very slightly yellow	solubility water: 50 mg/mL, clear to slightly hazy, colorless to light yellow	solubility DMSO: 50 mg/mL, clear, colorless to very faintly yellow	solubility DMSO: 50 mg/mL, clear, colorless to faintly yellow
suitability suitable for fluorescence	suitability -	suitability suitable for fluorescence	suitability -
form powder	form powder	form powder or crystals	form powder
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
fluorescence λ_ex 315 nm; λ_em 374 nm (pH.7.0), λ_ex 365 nm; λ_em 445 nm (after cleavage by neuraminidase)	fluorescence -	fluorescence λ_ex 365 nm; λ_em 445 nm in 0.1 M phosphate pH 6.5	fluorescence λ_ex 316 nm; λ_em 375 nm (Reaction product), λ_ex 317 nm; λ_em 374 nm (pH9.0), λ_ex 360 nm; λ_em 449 nm, λ_ex 365 nm; λ_em 445 nm in 0.1 M Tris pH 8.0 (α-glucosidase)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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