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D9050

Sigma-Aldrich

N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid

≥93% (TLC)

Synonym(s):

2,3-Dehydro-2-deoxy-N-acetylneuraminic acid

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About This Item

Empirical Formula (Hill Notation):
C11H17NO8
CAS Number:
24967-27-9
Molecular Weight:
291.25
Beilstein:
8722455
EC Number:
246-550-7
MDL number:
MFCD00135810
UNSPSC Code:
12352201
PubChem Substance ID:
24894248
NACRES:
NA.25

biological source

synthetic (organic)

Assay

≥93% (TLC)

form

powder

optical activity

[α]20/D 40.8 to 51.0 °, c = 0.66% (w/v) in water

color

white

solubility

H2O: soluble 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CC(=O)N[C@@H]1[C@@H](O)C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O

InChI

1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1

InChI key

JINJZWSZQKHCIP-UFGQHTETSA-N

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Application

N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid (NADNA), a specific endogenous neuraminidase (NEU) inhibitor, may be used to study the roles of endogenous neuraminidase in the development and function of neural processes and pathways as well as other processes that depend upon sialylation-desialylation cycles.

Biochem/physiol Actions

Inhibitor of bacterial, viral and animal neuraminidase (sialidase).

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

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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E Schreiner et al.
Carbohydrate research, 216, 61-66 (1991-09-02)
2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn
Elena Isaeva et al.
The European journal of neuroscience, 32(11), 1889-1896 (2010-11-04)
Polysialic acids are widely distributed in neuronal tissue. Due to their position on glycoproteins and gangliosides on the outer cell membranes and anionic nature, polysialic acids are involved in multiple cell signaling events. The level of sialylation of the cellular
Satoshi Uchiyama et al.
The Journal of experimental medicine, 206(9), 1845-1852 (2009-08-19)
In humans, Streptococcus pneumoniae (SPN) is the leading cause of bacterial meningitis, a disease with high attributable mortality and frequent permanent neurological sequelae. The molecular mechanisms underlying the central nervous system tropism of SPN are incompletely understood, but include a
Leonard M G Chavas et al.
Journal of medicinal chemistry, 53(7), 2998-3002 (2010-03-13)
With the global spread of the pandemic H1N1 and the ongoing pandemic potential of the H5N1 subtype, the influenza virus represents one of the most alarming viruses spreading worldwide. The influenza virus sialidase is an effective drug target, and a
Wen-Hsien Wen et al.
Bioorganic & medicinal chemistry, 18(11), 4074-4084 (2010-05-11)
Unlike the group-2 neuraminidase, the group-1 neuraminidase of influenza virus possesses a flexible loop (the 150-loop) and a cavity (the 150-cavity) adjacent to the active site, and renders a conformational change from the 'open' form to the 'closed' form on
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