X-Neu5Ac

• CAT Number: I002037
• CAS Number: 160369-85-7
• Molecular Formula: C19H21BrClN2NaO9
• Molecular Weight: 559.72
• Purity: ≥95%
• Solubility: 10 mM in DMSO
• Storage: Store at RT
• 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
• 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
• InChIKey: MNWWXEDVLXNFDD-GNZCRVNMSA-M
• SMILES: CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)[O-])OC2=CNC3=C2C(=C(C=C3)Br)Cl)O.[Na+]

X-Neu5Ac (Cat.No:I002037) is a significant sialic acid derivative with promising biomedical implications. Its distinct chemical structure has sparked interest among scientists for potential therapeutic applications. X-Neu5Ac’s role in cell communication and immunological processes makes it a fascinating target for research in areas such as cancer, inflammation, and infectious diseases.

Reference

1:Bioorg Med Chem. 1993 Aug;1(2):147-9. X-Neu5Ac: a novel substrate for chromogenic assay of neuraminidase activity in bacterial expression systems.Fujii I,Iwabuchi Y,Teshima T,Shiba T,Kikuchi M, PMID: 8081844 Abstract: A chromogenic substrate 1, 5-bromo-4-chloroindol-3-yl 5-acetamido-3,5-dideoxy-alpha-D-glycero-D-galacto-2-nonulopyranosidon ic acid (X-Neu5Ac), has been synthesized to facilitate the screening of bacterial colonies or plaques for the detection of either natural or mutant neuraminidase activity. Substrate 1 was hydrolyzed by neuraminidase isolated from Clostridium perfringens to release a halogenated indol-3-ol 2 that undergoes rapid aerobic oxidation to form the dark blue pigment, 5,5/’-dibromo-4,-4/’-dichloroindigo 3. 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 1 can be useful to screen for bacterially-encoded enzyme production directly on agar plates.