N-Acetyl-Neuraminic Acid

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Cat Number

PIPB-0763

CAS Number

131-48-6

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CAS Number

131-48-6

EINECS

205-023-1

Storage

Store at room temperature

Synonyms

N-acetylneuraminate; O-sialic acid; 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid

Molecular Formula

C11H19NO9

Molecular Weight

309.27

Smiles

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

Appearance

White to off-white solid powder

Melting Point

184-186°C (dec.)

Boiling Point

449.56°C (rough estimate)

Relative Density

1.3580 (rough estimate)

General Description

N-Acetylneuraminic acid (Neu5Ac) is the most prevalent and best-studied form of sialic acid. It is an abundant terminal monosaccharide of glycoconjugates on cell surfaces. Neu5Ac is a nutrient source for bacteria and, when displayed on the cell surface, serves as a binding site for host immune factors, viruses, and bacterial toxins.

Mechanism of Action

Sialic acids like Neu5Ac play crucial roles in various biological processes. They are involved in neurotransmission, leukocyte extravasation, and carbohydrate-protein recognition. As terminal sugars on cell surface glycoproteins and glycolipids, they are key determinants in cell-cell recognition and communication. The level of sialylation on cell surfaces is regulated through enzymatic removal by NEU enzymes. Clinically, it has been shown to possess potent antioxidant, anti-inflammatory, and anti-glycation properties.

Application

Neu5Ac is being investigated for its therapeutic potential, particularly in dermatology for skin brightening, hydration, and elasticity. It is also being studied for its role in immune function and has potential applications in infant formula and functional foods.

The mechanism of oxidative deamination of N‑nitroso‑N‑acetyl sialyl glycosides to KDN glycosides with overall retention of configuration was studied. No evidence was found for stereodirecting participation by ester groups at the 4‑ and 7‑positions. A common mechanism involving 1‑oxabicyclo[3.1.0]hexyl oxonium ion intermediates following pyranoside ring oxygen participation is proposed. In β‑thiosialosides, a minor pathway involves 4‑O‑acetyl exchange with glacial acetic acid, proposed to occur via thioglycoside participation at the diazoalkane stage.

Fig. 1 Synthesis of NeuAc Derivatives Selectively Functionalized at the 4-Position. (Buda S, Crich D, 2016)

References

Buda S, Crich D. Oxidative Deamination of N-Acetyl Neuraminic Acid: Substituent Effects and Mechanism. J Am Chem Soc. 2016;138(3):1084-1092.

A method combining metabolic labeling, click chemistry, 16S rRNA gene sequencing, and whole‑genome sequencing was developed to track and identify sialic acid (SA)‑presenting microbes in complex microbiomes. Using this approach, a new E. coli strain was isolated that incorporates SA onto its surface and encodes nanT, neuA, and neuS genes for SA harvesting and presentation. This method is applicable to identifying SA‑presenting bacteria from human, animal, and environmental microbiomes.

Fig. 2 Metabolic labeling and isolation of SA-presenting microbes from a fecal microbiome sample. (Han Z, et al., 2021)

References

Han Z, et al. Identification of an N-acetylneuraminic acid-presenting bacteria isolated from a human microbiome. Sci Rep. 2021;11(1):4763.

Does N-Acetyl-Neuraminic Acid require protection from light during long-term storage?

Yes, it is moderately photosensitive. Prolonged UV exposure can cause discoloration and degradation of the pyranose ring. Store in light-resistant containers.

What is the recommended storage temperature for N-Acetyl-Neuraminic Acid?

Store at 2-8°C (refrigerated). At room temperature, slow epimerization and decarboxylation may occur over extended periods.

Is N-Acetyl-Neuraminic Acid hygroscopic, and how is this managed?

It is moderately hygroscopic. Under high humidity (>60% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity N-acetylmannosamine (epimerization product) monitored?

This epimerization product is quantified using a stability-indicating HPLC method with refractive index or mass spectrometric detection.