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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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Sadagopan Magesh et al.
Bioorganic & medicinal chemistry, 17(13), 4595-4603 (2009-05-20)
Recent advances in the sialidase biology have clarified the role of human sialidases (NEU 1 to NEU4) in the development of various disease states such as cancer, diabetes and arteriosclerosis. Isoform selective human sialidase inhibitors could be a therapeutic tool
Keiko Hata et al.
Antimicrobial agents and chemotherapy, 52(10), 3484-3491 (2008-08-13)
Oseltamivir (Tamiflu) and zanamivir (Relenza), two extensively used clinically effective anti-influenza drugs, are viral sialidase (also known as neuraminidase) inhibitors that prevent the release of progeny virions and thereby limit the spread of infection. Recently mortalities and neuropsychiatric events have
Thomas Haselhorst et al.
Glycobiology, 17(1), 68-81 (2006-09-16)
The VP8* subunit of rotavirus spike protein VP4 contains a sialic acid (Sia)-binding domain important for host cell attachment and infection. In this study, the binding epitope of the N-acetylneuraminic acid (Neu5Ac) derivatives has been characterized by saturation transfer difference
Hisaaki Aoki et al.
Pediatrics international : official journal of the Japan Pediatric Society, 55(6), e143-e145 (2013-12-18)
Hemolytic uremic syndrome (HUS) in children is usually caused by Shiga-like toxin-producing Escherichia coli, but approximately 5% of cases are caused by invasive pneumococcal infection (P-HUS). Reported herein is the case of a 9-month-old HUS patient with pneumococcal meningitis who
Santosh Rudrawar et al.
Organic & biomolecular chemistry, 10(43), 8628-8639 (2012-09-15)
Novel 3-C-alkylated-Neu5Ac2en derivatives have been designed to target the expanded active site cavity of influenza virus sialidases with an open 150-loop, currently seen in X-ray crystal structures of influenza A virus group-1 (N1, N4, N5, N8), but not group-2 (N2
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