G9793
N-Glycolylneuraminic acid
≥95% (HPLC), semisynthetic
Sinónimos:
Neu5Glc, NeuNGl
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About This Item
Fórmula empírica (notación de Hill):
C11H19NO10
Número de CAS:
Peso molecular:
325.27
Beilstein/REAXYS Number:
1716828
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
Productos recomendados
biological source
semisynthetic
Quality Level
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
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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
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
For additional information on our range of Biochemicals, please complete this form.
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Comparable product
Referencia del producto
Descripción
Precios
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Certificados de análisis (COA)
Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»
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Los clientes también vieron
Potential impact of the non-human sialic acid N-glycolylneuraminic acid on transplant rejection risk.
Vered Padler-Karavani et al.
Xenotransplantation, 18(1), 1-5 (2011-02-24)
Xing Yu et al.
Journal of virology, 86(24), 13456-13466 (2012-10-05)
The rotavirus spike protein domain VP8* is essential for recognition of cell surface carbohydrate receptors, notably those incorporating N-acylneuraminic acids (members of the sialic acid family). N-Acetylneuraminic acids occur naturally in both animals and humans, whereas N-glycolylneuraminic acids are acquired
Nobuyoshi Hayashi et al.
Cancer science, 104(1), 43-47 (2012-09-26)
Gangliosides are glycosphingolipids found on the cell surface. They act as recognition molecules or signal modulators and regulate cell proliferation and differentiation. N-glycolylneuraminic acid (NeuGc)-containing gangliosides have been detected in some neoplasms in humans, although they are usually absent in
Eiki Maeda et al.
Analytical chemistry, 84(5), 2373-2379 (2012-03-08)
Minor N-linked glycans containing N-glycolylneuraminic acid residues and/or α-Gal epitopes (i.e., galactose-α1,3-galactose residues) have been reported to be present in recombinant monoclonal antibody (mAb) therapeutics. These contaminations are due to their production processes using nonhuman mammalian cell lines in culture
Nabin B Basnet et al.
Xenotransplantation, 17(6), 440-448 (2010-12-17)
A number of carbohydrate structures apart from Galα1-3Galβ1-4GlcNAc (Gal) have been implicated as potential xenoantigens. Epitopes of another carbohydrate structure, namely N-glycolylneuraminic acid (NeuGc), are widely expressed on the surfaces of endothelial cells of all mammals, except humans, and are
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