G9793
N-Glycolylneuraminic acid
≥95% (HPLC), semisynthetic
Synonym(s):
Neu5Glc, NeuNGl
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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C11H19NO10
CAS Number:
Molecular Weight:
325.27
Beilstein/REAXYS Number:
1716828
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
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
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Certificates of Analysis (COA)
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Customers Also Viewed
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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