X-NeuNAc

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Catalog No: A10GD-4360
Cas No: 160369-85-7
Properties: Mol Formula: C19H21BrClN2NaO9, Mol Weight: 559.7
IUPAC Name: sodium;(2S,4S,5R,6R)-5-acetamido-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
Synonym: X-Neu5Ac, 5-Bromo-4-chloro-3-indolyl-alpha-D-N-acetylneuraminic acid sodium salt, SODIUM (2S,4S,5R,6R)-2-[(5-BROMO-4-CHLORO-1H-INDOL-3-YL)OXY]-5-ACETAMIDO-4-HYDROXY-6-[(1R,2R)-1,2,3-TRIHYDROXYPROPYL]OXANE-2-CARBOXYLATE

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Description

5-Bromo-4-chloro-3-indolyl N-acetyl-a-D-neuraminic acid sodium salt

X-NeuNAc is a chromogenic substrate for neuraminidases, which are enzymes that cleave glycosidic linkages of neuraminic acids. Upon hydrolysis by neuraminidase, halogenated indol-3-ol is released and undergoes rapid aerobic oxidation to the dark blue pigment 5,5?-dibromo-4-4?-dichloroindigo, which can be used to quantify neuraminidase activity.

X-NeuNAc, also known as CB1339 and X-Neu5Ac, is a novel substrate for chromogenic assay of neuraminidase activity in bacterial expression systems. X-NeuNAc can be used to facilitate the screening of bacterial colonies or plaques for the detection of either natural or mutant neuraminidase activity. Preliminary kinetic studies indicate that this compound is a good substrate (Km 0.89 x 10(-3) M) for neuraminidase and is quite stable under identical conditions in the absence of enzyme. These results suggest that X-Neu5Ac can be useful to screen for bacterially-encoded enzyme production directly on agar plates.

Chromogenic substrate for neuraminidase yielding a blue precipitate upon cleavage.

CAS Number 160369-85-7
Product Name X-NeuNAc
IUPAC Name sodium;(2S,4S,5R,6R)-5-acetamido-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
Molecular Formula C19H21BrClN2NaO9
Molecular Weight 559.7258
InChI InChI=1S/C19H22BrClN2O9.Na/c1-7(25)23-15-10(26)4-19(18(29)30,32-17(15)16(28)11(27)6-24)31-12-5-22-9-3-2-8(20)14(21)13(9)12;/h2-3,5,10-11,15-17,22,24,26-28H,4,6H2,1H3,(H,23,25)(H,29,30);/q;+1/p-1/t10-,11+,15+,16+,17+,19+;/m0./s1
InChI Key MNWWXEDVLXNFDD-GNZCRVNMSA-M
SMILES CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)[O-])OC2=CNC3=C2C(=C(C=C3)Br)Cl)O.[Na+]
Solubility Soluble in DMSO
Synonyms X-Neu5Ac; CB-1339; 160369-85-7; X-NeuNAc.


CAS No: 160369-85-7
Synonyms: X-NANA.Na
MDL No: MFCD00792680 
 Chemical Formula: C19H21BrClN2O9?Na
Molecular Weight: 559.72


References:
1. Fujii I, et al., Bioorg. Med. Chem. 1993, 1, p147

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Size

1 G, 100 MG, 5 G, Other

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