G9793

N-Glycolylneuraminic acid

≥95% (HPLC), semisynthetic

• Synonym(s): Neu5Glc, NeuNGl
• Empirical Formula (Hill Notation): C₁₁H₁₉NO₁₀
• CAS Number: 1113-83-3
• Molecular Weight: 325.27
• UNSPSC Code: 12352201
• NACRES: NA.25
• PubChem Substance ID: 24895382
• MDL number: MFCD00057551
• Beilstein/REAXYS Number: 1716828

Properties

• biological source: semisynthetic
• Quality Segment: 200
• assay: ≥95% (HPLC)
• form: powder
• technique(s): LC/MS: suitable
• impurities: water (Karl Fischer)
• color: white
• solubility: water: soluble 20 mg/mL
• suitability: suitable for LC-MS
• application(s): metabolomics
• storage temp.: −20°C
• SMILES string: [H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(=O)CO)C(O)=O)[C@H](O)[C@H](O)CO
• 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

Description

General description

N-Glycolylneuraminic acid (Neu5Gc) is a nonhuman sialic acid molecule synthesized in pigs but not in humans, that has a role as a mammalian metabolite and an antigen. This hydroxylated form of sialic acid, specifically N-acetylneuraminic acid, features a glycolyl substituent on nitrogen and a beta-configuration at the anomeric center. The biosynthesis of N-glycolylneuraminic acid involves the enzymatic activity of cytidine monophosphate-N-acetylneuraminate (CMP-Neu5Ac) hydroxylase.
In humans, the absence of endogenous production results from a gene mutation affecting CMP-Neu5Ac hydroxylase, the enzyme responsible for converting N-acetylneuraminic acid into Neu5Gc. However, Neu5Gc can accumulate in human cells through external ingestion from dietary sources like red meat and dairy products. N-Glycolylneuraminic acid is a versatile compound that finds application in cell biology, metabolomics and biochemical research

Application

N-Glycolylneuraminic acid has been used:

• as a sugar in microtiter biofilm methodologic approach for the enhancement of biofilm formation
• as a standard for the determination of sialic acids in the nervous system of silkworm and to find the variations of sialic acids among different developmental stages.
• as a standard in the high-performance liquid chromatography (HPLC) analyses to detect the molecular species of sialic acid (Sia) species using 1,2-diamino-4,5-methylenedioxy-benzene (DMB) as a fluorogenic compound

Biochem/physiol Actions

N-Glycolylneuraminic acid (Neu5Gc) functions as an important tool for profiling anti-Neu5Gc antibodies and sialic acid-binding proteins.

Features and Benefits

• Ideal for Metabolomics, Biochemical and Cell Biology research
• Versatile and adaptable for wide variety of laboratory and research applications

Other Notes

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To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)