N-Glycolylneuraminic acid

• CAS: 1113-83-3
• Catalog Number: ACM1113833
• Category: Main Products
• Molecular Weight: 325.27
• Molecular Formula: C11H19NO10
• Synonyms: Neu5Gc
• IUPAC Name: (2S,4S,5R,6R)-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Canonical SMILES: C1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O
• InChI: InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1
• InChI Key: FDJKUWYYUZCUJX-AJKRCSPLSA-N
• Boiling Point: 884.2ºC at 760 mmHg
• Melting Point: 188-190 °C
• Flash Point: 488.6ºC
• Density: 1.670±0.06 g/ml
• Appearance: White to off-white powder
• Exact Mass: 325.10100
• pKa: 2.41±0.54
• Solubility In Water: Sparingly
• WGK Germany: 3

Case Study

Synthesis of N-Glycolneuraminic Acid and Its Glycosides

Anoopjit Singh Kooner, et al. Frontiers in immunology, 2019, 10, 451547.

N-Glycolylneuraminic acid (Neu5Gc) is one of the most common forms of sialic acid found in nature. The one-pot multi-enzyme (OPME) chemoenzyme method is an efficient synthetic strategy for Neu5Gc-sialoside and its derivatives, which can be used to synthesize Neu5Gc simple glycosides, Neu5Gc-containing oligosaccharides, Neu5Gc-containing oligosaccharides, and Neu5Gc-containing glycoconjugates.
Synthesis example of Neu5Gc simple glycoside
· Simple glycosides of Neu5Gc were synthesized from the corresponding Neu5Ac derivatives by direct de-N-acetylation of the N-acetyl group of Neu5Ac under strongly basic conditions, followed by acylation and deprotection.
· Example A: To create the allyl α-Neu5Gc-glycoside, the N-acetyl group was removed from the carboxyl protected allyl α-Neu5Ac-glycoside through refluxing in tetramethylammonium hydroxide, resulting in an 80% yield. The next steps involved acylation with acetoxyacetyl chloride and hydrolysis of the ester.
· Example B: The methyl α-Neu5Ac glycoside was subjected to treatment with 2.0 M of NaOH using optimized microwave irradiation conditions, resulting in the desired 5-amino derivative with a yield of 91%. Subsequently, the resulting compound was transformed into the target methyl α-Neu5Gc glycoside (Neu5GcαOMe) through a reaction with acetoxyacetyl chloride, followed by de-O-acetylation.

N-Glycolylneuraminic Acid on Biotherapeutics Associated with Their Production System

Sharon Yehuda, et al. Frontiers in immunology, 2020, 11, 502962.

The production of many biotherapeutics involves non-human mammalian cells, serum, or serum-derived substances and therefore may contain certain levels of N-glycolylneuraminic acid (Neu5Gc). Production systems for biotherapeutics related to Neu5Gc have been widely reported. Listed below are some Neu5Gc-related biotherapeutics and their production systems.
· Chinese hamster ovary (CHO) cells are the most common biotherapeutic platform. Several studies have shown the presence of Neu5Gc in biotherapeutics produced by CHO cells, but at relatively low levels.
· Baby hamster kidney cells (BHK-21) are also frequently used to produce biotherapeutics and are expected to express low levels of Neu5Gc.
· Murine myeloma cell lines such as NS0 and Sp2/0 are known to produce Neu5Gc at significantly higher levels.
· Drugs derived from animals that naturally produce Neu5Gc, such as cows, pigs, goats, sheep, and rabbits, are likely to also contain Neu5Gc because these animals have been found to have high levels of Neu5Gc.
· It is possible for human cells to also produce biotherapeutics containing Neu5Gc if Neu5Gc is accidentally introduced into their growth environment, such as through the use of animal serum or serum-derived products.