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

For research use only. Not for therapeutic Use.

  • CAT Number: R066672
  • CAS Number: 24967-27-9
  • Molecular Formula: C11H17NO8
  • Molecular Weight: 291.25
  • Purity: ≥95%
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N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid shows inhibitory activities against human neuraminidase enzymes with IC50s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity[1][2].
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells[4].
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10?mg/kg; i.p.; daily) attenuates pulmonary fibrosis in a mouse model[3].


Catalog Number R066672
CAS Number 24967-27-9
Synonyms

(2R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

Molecular Formula C11H17NO8
Purity ≥95%
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
InChIKey JINJZWSZQKHCIP-KLBWXOEVSA-N
SMILES CC(=O)NC1C(C=C(OC1C(C(CO)O)O)C(=O)O)O
Reference

[1]. Magesh S, et al. Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1). Bioorg Med Chem Lett. 2008;18(2):532-537.
 [Content Brief]

[2]. Xiao A, et al. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors. ACS Catal. 2018;8(1):43-47.
 [Content Brief]

[3]. Karhadkar TR, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8.
 [Content Brief]

[4]. Minami A, et al. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion. Sci Rep. 2020;10(1):5198. Published 2020 Mar 23.
 [Content Brief]

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