G9793
N-Glycolylneuraminic acid
N-Glycolylneuraminic acid
≥95% (HPLC), semisynthetic
Sinónimos:
Neu5Glc, NeuNGl
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10 MG
US$ 628,00
25 MG
US$ 1.250,00
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10 MG
US$ 628,00
25 MG
US$ 1.250,00
About This Item
Fórmula empírica (notación de Hill):
C11H19NO10
Número de CAS:
Peso molecular:
325.27
Beilstein:
1716828
Número MDL:
Código UNSPSC:
12352201
ID de la sustancia en PubChem:
NACRES:
NA.25
Productos recomendados
origen biológico
semisynthetic
Nivel de calidad
Ensayo
≥95% (HPLC)
Formulario
powder
técnicas
LC/MS: suitable
impurezas
water (Karl Fischer)
color
white
solubilidad
water: soluble 20 mg/mL
idoneidad
suitable for LC-MS
aplicaciones
metabolomics
temp. de almacenamiento
−20°C
cadena 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
Clave InChI
FDJKUWYYUZCUJX-AJKRCSPLSA-N
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Descripción general
N-Glycolylneuraminic acid (Neu5Gc) is a nonhuman sialic acid[1] 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
Aplicación
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
Acciones bioquímicas o fisiológicas
N-Glycolylneuraminic acid (Neu5Gc) functions as an important tool for profiling anti-Neu5Gc antibodies and sialic acid-binding proteins.
Características y beneficios
- Ideal for Metabolomics, Biochemical and Cell Biology research
- Versatile and adaptable for wide variety of laboratory and research applications
Otras 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.
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Referencia del producto
Descripción
Precios
Código de clase de almacenamiento
11 - Combustible Solids
Clase de riesgo para el agua (WGK)
WGK 3
Punto de inflamabilidad (°F)
Not applicable
Punto de inflamabilidad (°C)
Not applicable
Equipo de protección personal
Eyeshields, Gloves, type N95 (US)
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Los clientes también vieron
Chao-Tan Guo et al.
Glycobiology, 17(7), 713-724 (2007-03-29)
The receptor specificity of influenza viruses is one factor that allows avian influenza viruses to cross the species barrier. The recent transmissions of avian H5N1 and H9N2 influenza viruses from chickens and/or quails to humans indicate that avian influenza viruses
Anoopjit Singh Kooner et al.
Frontiers in immunology, 10, 2004-2004 (2019-09-27)
Sialic acids constitute a family of negatively charged structurally diverse monosaccharides that are commonly presented on the termini of glycans in higher animals and some microorganisms. In addition to N-acetylneuraminic acid (Neu5Ac), N-glycolyl neuraminic acid (Neu5Gc) is among the most
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
Dzung H Nguyen et al.
Journal of immunology (Baltimore, Md. : 1950), 175(1), 228-236 (2005-06-24)
Humans are genetically incapable of producing the mammalian sialic acid N-glycolylneuraminic acid (Neu5Gc), due to an inactivating mutation in the enzyme synthesizing it. Despite this, human cells and tissues appear capable of metabolically incorporating Neu5Gc from exogenous sources, including dietary
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
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