G9793
N-Glycolylneuraminic acid
≥95% (HPLC), semisynthetic
Sinônimo(s):
Neu5Glc, NeuNGl
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About This Item
Fórmula empírica (Notação de Hill):
C11H19NO10
Número CAS:
Peso molecular:
325.27
Beilstein:
1716828
Número MDL:
Código UNSPSC:
12352201
ID de substância PubChem:
NACRES:
NA.25
Produtos recomendados
fonte biológica
semisynthetic
Nível de qualidade
Ensaio
≥95% (HPLC)
forma
powder
técnica(s)
LC/MS: suitable
Impurezas
water (Karl Fischer)
cor
white
solubilidade
water: soluble 20 mg/mL
adequação
suitable for LC-MS
aplicação(ões)
metabolomics
temperatura de armazenamento
−20°C
cadeia de caracteres SMILES
[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
chave InChI
FDJKUWYYUZCUJX-AJKRCSPLSA-N
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Descrição geral
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
Aplicação
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
Ações bioquímicas/fisiológicas
N-Glycolylneuraminic acid (Neu5Gc) functions as an important tool for profiling anti-Neu5Gc antibodies and sialic acid-binding proteins.
Características e benefícios
- Ideal for Metabolomics, Biochemical and Cell Biology research
- Versatile and adaptable for wide variety of laboratory and research applications
Outras notas
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.
produto comparável
Nº do produto
Descrição
Preços
Código de classe de armazenamento
11 - Combustible Solids
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
Equipamento de proteção individual
Eyeshields, Gloves, type N95 (US)
Certificados de análise (COA)
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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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