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N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid - ≥93%, high purity , CAS No.24967-27-9

≥93%

CAS#: 24967-27-9
Formula: C₁₁H₁₇NO₈
Molecular Weight: 291.26
MDL number: MFCD00135810
PubChem CID: 65309

Item Number

N463295

Grouped product items
SKU	Size	Availability	Price
N463295-5mg	5mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$169.90
N463295-10mg	10mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$319.90
N463295-25mg	25mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$759.90

View related series

Anti-infection Influenza Virus

Basic Description

Synonyms	5-N-Acetyl-2-deoxy-2,3-didehydro-neuraminic acid\|Neu2en5Ac\|24967-27-9\|Neu5Ac2en\|DANA\|2-Deoxy-2,3-dehydro-N-acetylneuraminic acid\|2,3-Dehydro-2-deoxy-N-acetylneuraminic acid\|1,3-Dehydro-2-deoxy-N-acetylneuraminicacid\|N-Acetyl-2,3-dehydro-2-deoxyneuraminic
Specifications & Purity	≥93%
Biochemical and Physiological Mechanisms	Inhibitor of bacterial, viral and animal neuraminidase (sialidase).
Storage Temp	Protected from light,Store at -20°C
Shipped In	Ice chest + Ice pads
Product Description	Description 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.

Associated Targets

NEU4 Tchem Sialidase-4 1 Activities

Discover Target: NEU4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NEU2 Tbio Sialidase-2 0 Activities

Discover Target: NEU2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NEU1 Tchem Sialidase-1 0 Activities

Discover Target: NEU1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NEU3 Tchem Sialidase-3 0 Activities

Discover Target: NEU3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Names and Identifiers

IUPAC Name	(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
INCHI	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
Canonical SMILES	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
Isomeric 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)O
PubChem CID	65309
Molecular Weight	291.26

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Solubility	H2O: soluble 50mg/mL, clear, colorless
Sensitivity	Light sensitive
Melt Point(°C)	134°C(lit.)

Alternative Products

References

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17. Yao Zou,Amgad Albohy,Mahendra Sandbhor,Christopher W Cairo. (2010-11-03) Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid.. Bioorganic & medicinal chemistry letters, 20 ((24)): (7529-7533). [PMID:21036040]
18. Elena Isaeva,Irina Lushnikova,Alina Savrasova,Galina Skibo,Gregory L Holmes,Dmytro Isaev. (2010-11-04) Blockade of endogenous neuraminidase leads to an increase of neuronal excitability and activity-dependent synaptogenesis in the rat hippocampus.. The European journal of neuroscience, 32 ((11)): (1889-1896). [PMID:21044183]
19. Masahiro Takaguchi,Tadanobu Takahashi,Chika Hosokawa,Hiroo Ueyama,Keijo Fukushima,Takuya Hayakawa,Kazuhiko Itoh,Kiyoshi Ikeda,Takashi Suzuki. (2010-12-28) A single amino acid mutation at position 170 of human parainfluenza virus type 1 fusion glycoprotein induces obvious syncytium formation and caspase-3-dependent cell death.. Journal of biochemistry, 149 ((2)): (191-202). [PMID:21186250]
20. Reiko Nishino,Kiyoshi Ikeda,Takuya Hayakawa,Tadanobu Takahashi,Takashi Suzuki,Masayuki Sato. (2011-03-09) Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1.. Bioorganic & medicinal chemistry, 19 ((7)): (2418-2427). [PMID:21382718]
21. Irina V Alymova,Allen Portner,Vasiliy P Mishin,Jonathan A McCullers,Pamela Freiden,Garry L Taylor. (2011-08-19) Receptor-binding specificity of the human parainfluenza virus type 1 hemagglutinin-neuraminidase glycoprotein.. Glycobiology, 22 ((2)): (174-180). [PMID:21846691]
22. Alan S Cross,Sang Won Hyun,Alba Miranda-Ribera,Chiguang Feng,Anguo Liu,Chinh Nguyen,Lei Zhang,Irina G Luzina,Sergei P Atamas,William S Twaddell,Wei Guang,Erik P Lillehoj,Adam C Puché,Wei Huang,Lai-Xi Wang,Antonino Passaniti,Simeon E Goldblum. (2012-03-10) NEU1 and NEU3 sialidase activity expressed in human lung microvascular endothelia: NEU1 restrains endothelial cell migration, whereas NEU3 does not.. The Journal of biological chemistry, 287 ((19)): (15966-15980). [PMID:22403397]
23. Chiguang Feng,Nicholas M Stamatos,Anatoliy I Dragan,Andrei Medvedev,Melissa Whitford,Lei Zhang,Chang Song,Prasad Rallabhandi,Leah Cole,Quan M Nhu,Stefanie N Vogel,Chris D Geddes,Alan S Cross. (2012-04-13) Sialyl residues modulate LPS-mediated signaling through the Toll-like receptor 4 complex.. PloS one, 7 ((4)): (e32359-e32359). [PMID:22496731]
24. Tomoko Nishikawa,Kazufumi Shimizu,Torahiko Tanaka,Kazumichi Kuroda,Tadatoshi Takayama,Tatsuo Yamamoto,Nobuhiro Hanada,Yoshiki Hamada. (2012-10-03) Bacterial neuraminidase rescues influenza virus replication from inhibition by a neuraminidase inhibitor.. PloS one, 7 ((9)): (e45371-e45371). [PMID:23028967]
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28. Amandine Scandolera,Fanja Rabenoelina,Carine Chaintreuil,Anthony Rusciani,Pascal Maurice,Sébastien Blaise,Béatrice Romier-Crouzet,Hassan El Btaouri,Laurent Martiny,Laurent Debelle,Laurent Duca. (2015-06-19) Uncoupling of Elastin Complex Receptor during In Vitro Aging Is Related to Modifications in Its Intrinsic Sialidase Activity and the Subsequent Lactosylceramide Production.. PloS one, 10 ((6)): (e0129994-e0129994). [PMID:26086247]
29. Darrell Pilling,Tejas R Karhadkar,Richard H Gomer. (2020-12-31) A CD209 ligand and a sialidase inhibitor differentially modulate adipose tissue and liver macrophage populations and steatosis in mice on the Methionine and Choline-Deficient (MCD) diet.. PloS one, 15 ((12)): (e0244762-e0244762). [PMID:33378413]
30. Kiyoshi Ikeda,Kazuki Sato,Satoru Kitani,Takashi Suzuki,Naoyoshi Maki,Yasuo Suzuki,Masayuki Sato. (2006-08-16) 2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogues structurally modified at the C-4 position: synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1.. Bioorganic & medicinal chemistry, 14 ((23)): (7893-7897). [PMID:16908163]
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32. Evan J Horn,Jonel P Saludes,Jacquelyn Gervay-Hague. (2008-02-20) Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers.. Carbohydrate research, 343 ((5)): (936-940). [PMID:18282561]
33. Kiyoshi Ikeda,Kazuki Sato,Reiko Nishino,Shinya Aoyama,Takashi Suzuki,Masayuki Sato. (2008-06-17) 2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogs structurally modified by thiocarbamoylalkyl groups at the C-4 position: Synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1.. Bioorganic & medicinal chemistry, 16 ((14)): (6783-6788). [PMID:18555688]
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37. A V Savrasova,I V Lushnikova,E V Isaeva,G G Skibo,D S Isaev,P G Kostyuk. (2010-10-23) The effect of neuraminidase blocker on gabazine-induced seizures in rat hippocampus.. Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994), 56 ((4)): (14-18). [PMID:20964139]
38. Amgad Albohy,Sankar Mohan,Ruixiang Blake Zheng,B Mario Pinto,Christopher W Cairo. (2011-04-15) Inhibitor selectivity of a new class of oseltamivir analogs against viral neuraminidase over human neuraminidase enzymes.. Bioorganic & medicinal chemistry, 19 ((9)): (2817-2822). [PMID:21489803]
39. Susan Barrett,Peter G Mohr,Peter M Schmidt,Jennifer L McKimm-Breschkin. (2011-08-23) Real time enzyme inhibition assays provide insights into differences in binding of neuraminidase inhibitors to wild type and mutant influenza viruses.. PloS one, 6 ((8)): (e23627-e23627). [PMID:21858186]
40. Anderson H Lima,Paulo R M Souza,Nelson Alencar,Jerônimo Lameira,Thavendran Govender,Hendrik G Kruger,Glenn E M Maguire,Cláudio N Alves. (2012-03-16) Molecular modeling of T. rangeli, T. brucei gambiense, and T. evansi sialidases in complex with the DANA inhibitor.. Chemical biology & drug design, 80 ((1)): (114-120). [PMID:22416952]
41. Santosh Rudrawar,Philip S Kerry,Marie-Anne Rameix-Welti,Andrea Maggioni,Jeffrey C Dyason,Faith J Rose,Sylvie van der Werf,Robin J Thomson,Nadia Naffakh,Rupert J M Russell,Mark von Itzstein. (2012-09-15) Synthesis and evaluation of novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility.. Organic & biomolecular chemistry, 10 ((43)): (8628-8639). [PMID:22976385]
42. Donald F Smee,Mark von Itzstein,Beenu Bhatt,E Bart Tarbet. (2012-10-03) Exacerbation of influenza virus infections in mice by intranasal treatments and implications for evaluation of antiviral drugs.. Antimicrobial agents and chemotherapy, 56 ((12)): (6328-6333). [PMID:23027194]
43. Reiko Nishino,Takuya Hayakawa,Tadanobu Takahashi,Takashi Suzuki,Masayuki Sato,Kiyoshi Ikeda. (2013-01-11) Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by α-acylaminoamido groups at the C-4 position using isocyanide-based four-component coupling and biological evaluation as inhibitors of human parainfluenza virus type 1.. Chemical & pharmaceutical bulletin, 61 ((1)): (69-74). [PMID:23302587]
44. Kwang-Hyun Park,Min-Gyu Kim,Hee-Jeong Ahn,Dae-Han Lee,Jin-Hyo Kim,Young-Wan Kim,Eui-Jeon Woo. (2013-05-15) Structural and biochemical characterization of the broad substrate specificity of Bacteroides thetaiotaomicron commensal sialidase.. Biochimica et biophysica acta, 1834 ((8)): (1510-1519). [PMID:23665536]
45. Jihong Li,Bruce A McClane. (2014-08-20) Contributions of NanI sialidase to Caco-2 cell adherence by Clostridium perfringens type A and C strains causing human intestinal disease.. Infection and immunity, 82 ((11)): (4620-4630). [PMID:25135687]
46. Hung-Lun Hsu,Jean K Millet,Deirdre A Costello,Gary R Whittaker,Susan Daniel. (2016-10-19) Viral fusion efficacy of specific H3N2 influenza virus reassortant combinations at single-particle level.. Scientific reports, 6 (35537-35537). [PMID:27752100]
47. Tejas R Karhadkar,Darrell Pilling,Nehemiah Cox,Richard H Gomer. (2017-11-10) Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model.. Scientific reports, 7 ((1)): (15069-15069). [PMID:29118338]

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