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MA00746

N-Acetylneuraminic acid

Biologically relevant in neurotransmission and carbohydrate-protein recognition

Technical Data

CAS No: 131-48-6
Synonyms: Sialic acid; NANA; Neu5Ac
Product Code: MA00746
MDL No: MFCD00006620
Chemical Formula: C11H19NO9
Molecular Weight: 309.27

References


  • Boons, GJ and Demchenko AV (2000). Recent advances in o-sialylation.Chem Rev 100(12):4539-66., Rahmann, H et al (1976). A functional model of sialo-glyco-macromolecules in synaptic transmission and memory formation. J Theor Biol 57: 231-237.
  • Eisenberg, EJ et al (1997). Penetration of GS4071, a novel influenza neuraminidase inhibitor, into rat bronchoalveolar lining fluid following oral administration of the prodrug GS4104. Antimicrob Agents Chemother 41(9):1949-52., Resende, R et al (2009). Palladium-catalysed allylic amination for the direct synthesis of epi-4-alkylamino-N-acetylneuraminic acid derivatives. Tetrahedron Lett 50(28): 4009-4011.
  • Ikeda, K et al (2002). Use of phenyl 2-alpha-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions. Bioorg Med Chem Lett 16:2618. Ikeda, K et al (2006). Novel glycosylation reactions using glycosyl thioimidates of N-acetylneuraminic acid as sialyl donors. Bioorg Med Chem Lett 16(10):2618-20., Szabó, ZB et al (2008). A first synthesis of sulfonic acid analogues of N-acetylneuraminic acid. Tetrahedron Letters 49(7):1196-1198.
  • Kobayashi, S et al (2002). Rare-earth metal triflates in organic synthesis. Chem Rev 102(6):2227-302., von Itzstein, M et al (1994). The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: a potent influenza virus sialidase inhibitor. Carbohydr Res 259(2):301-5.
  • Kolisis, FN (1986). An immobilized bienzyme system for assay of sialic acid. Biotechnol Appl Biochem 8(2-3):148-52., Wiggins, R et al (2000). Use of 5-Bromo-4-Chloro-3-Indolyl-α-d-N-Acetylneuraminic Acid in a Novel Spot Test To Identify Sialidase Activity in Vaginal Swabs from Women with Bacterial Vaginosis. J Clin Microbiol 38(8): 3096–3097.

Solubility

Stability

Further Information


Datasheets

Specification: View
MSDS: View
Technical Bulletin: View

N-Acetylneuraminic acid

CAS No:
131-48-6
Synonyms:
Sialic acid
NANA
Neu5Ac
MDL No:
MFCD00006620
Chemical Formula:
Molecular Weight:
309.27
Product Structure
References:
1. Boons, GJ and Demchenko AV (2000). Recent advances in o-sialylation.Chem Rev 100(12):4539-66., Rahmann, H et al (1976). A functional model of sialo-glyco-macromolecules in synaptic transmission and memory formation. J Theor Biol 57: 231-237.
2. Eisenberg, EJ et al (1997). Penetration of GS4071, a novel influenza neuraminidase inhibitor, into rat bronchoalveolar lining fluid following oral administration of the prodrug GS4104. Antimicrob Agents Chemother 41(9):1949-52., Resende, R et al (2009). Palladium-catalysed allylic amination for the direct synthesis of epi-4-alkylamino-N-acetylneuraminic acid derivatives. Tetrahedron Lett 50(28): 4009-4011.

3. Ikeda, K et al (2002). Use of phenyl 2-alpha-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions. Bioorg Med Chem Lett 16:2618.

Ikeda, K et al (2006). Novel glycosylation reactions using glycosyl thioimidates of N-acetylneuraminic acid as sialyl donors. Bioorg Med Chem Lett 16(10):2618-20., Szabó, ZB et al (2008). A first synthesis of sulfonic acid analogues of N-acetylneuraminic acid. Tetrahedron Letters 49(7):1196-1198.
4. Kobayashi, S et al (2002). Rare-earth metal triflates in organic synthesis. Chem Rev 102(6):2227-302., von Itzstein, M et al (1994). The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: a potent influenza virus sialidase inhibitor. Carbohydr Res 259(2):301-5.
5. Kolisis, FN (1986). An immobilized bienzyme system for assay of sialic acid. Biotechnol Appl Biochem 8(2-3):148-52., Wiggins, R et al (2000). Use of 5-Bromo-4-Chloro-3-Indolyl-α-d-N-Acetylneuraminic Acid in a Novel Spot Test To Identify Sialidase Activity in Vaginal Swabs from Women with Bacterial Vaginosis. J Clin Microbiol 38(8): 3096–3097.
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