M6405
2-O-Methyl-α-D-N-acetylneuraminic acid
~95% (TLC)
Synonym(s):
α-D-Neu-5-Ac-2→OCH3
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About This Item
Empirical Formula (Hill Notation):
C12H21NO9
CAS Number:
Molecular Weight:
323.30
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
Recommended Products
Assay
~95% (TLC)
storage temp.
−20°C
SMILES string
COC1(CC(O)C(NC(C)=O)C(O1)C(O)C(O)CO)C(O)=O
InChI
1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(21-2,11(19)20)22-10(8)9(18)7(17)4-14/h6-10,14,16-18H,3-4H2,1-2H3,(H,13,15)(H,19,20)
InChI key
NJRVVFURCKKXOD-UHFFFAOYSA-N
General description
N-acetylneuraminic acid is the minimum binding epitope of rotavirus to host cells.
Application
2-O-Methyl-α-D-N-acetylneuraminic acid is a model compound for studies assessing the binding of influenza virus hemagglutinin and metal ions. N-acetylneuraminic acid has been used in a study to assess lactose-based sialylmimetics inhibition of the rhesus and human rotavirus strains. It has also been used in a study to investigate the binding specificity of botulinum C16S toxin HA1 to various sugars.
Storage Class Code
13 - Non Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Daman, M.E., and Dill, K.
Carbohydrate Research, 102, 47-47 (1982)
Angela Liakatos et al.
Bioorganic & medicinal chemistry, 14(3), 739-757 (2005-10-11)
Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface
Toshio Nakamura et al.
Journal of molecular biology, 376(3), 854-867 (2008-01-08)
Clostridium botulinum type C 16S progenitor toxin contains a hemagglutinin (HA) subcomponent, designated HA1, which appears to play an important role in the effective internalization of the toxin in gastrointestinal epithelial cells and in creating a broad specificity for the
N K Sauter et al.
Biochemistry, 28(21), 8388-8396 (1989-10-17)
The equilibrium binding of influenza virus hemagglutinin to derivatives of its cell-surface ligand, sialic acid, was measured by nuclear magnetic resonance (NMR) spectroscopy. Binding was quantified by observing perturbations of sialic acid resonances in the presence of protein. The major
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