Ugrás a tartalomra
Merck

G9793

Sigma-Aldrich

N-Glycolylneuraminic acid

≥95% (HPLC), semisynthetic

Szinonimák:

Neu5Glc, NeuNGl

Bejelentkezésa Szervezeti és Szerződéses árazás megtekintéséhez


About This Item

Tapasztalati képlet (Hill-képlet):
C11H19NO10
CAS-szám:
Molekulatömeg:
325.27
Beilstein:
1716828
MDL-szám:
UNSPSC kód:
12352201
PubChem Substance ID:
NACRES:
NA.25

biológiai forrás

semisynthetic

Minőségi szint

Teszt

≥95% (HPLC)

Forma

powder

technika/technikák

LC/MS: suitable

szennyeződések

water (Karl Fischer)

szín

white

oldhatóság

water: soluble 20 mg/mL

alkalmasság

suitable for LC-MS

alkalmazás(ok)

metabolomics

tárolási hőmérséklet

−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

Nemzetközi kémiai azonosító kulcs

FDJKUWYYUZCUJX-AJKRCSPLSA-N

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Általános leírás

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

Alkalmazás

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

Biokémiai/fiziológiai hatások

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

Tulajdonságok és előnyök

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

Egyéb megjegyzések

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.

összehasonlítható termékek

Product No.
Leírás
Árazás

Tárolási osztály kódja

11 - Combustible Solids

WGK

WGK 3

Lobbanási pont (F)

Not applicable

Lobbanási pont (C)

Not applicable

Egyéni védőeszköz

Eyeshields, Gloves, type N95 (US)


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Analitikai tanúsítványok (COA)

Lot/Batch Number

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Dokumentumtár megtekintése

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
Vered Padler-Karavani et al.
PloS one, 8(3), e58443-e58443 (2013-03-23)
N-glycolylneuraminic acid (Neu5Gc) is an immunogenic sugar of dietary origin that metabolically incorporates into diverse native glycoconjugates in humans. Anti-Neu5Gc antibodies are detected in all human sera, though with variable levels and epitope-recognition profiles. These antibodies likely play a role
Alexandra S Gambaryan et al.
Journal of virology, 86(8), 4370-4379 (2012-02-22)
Influenza viruses of gallinaceous poultry and wild aquatic birds usually have distinguishable receptor-binding properties. Here we used a panel of synthetic sialylglycopolymers and solid-phase receptor-binding assays to characterize receptor-binding profiles of about 70 H7 influenza viruses isolated from aquatic birds
Jong-Yi Park et al.
Cellular reprogramming, 14(4), 353-363 (2012-07-11)
In this study, we examined whether Hanganutziu-Deicher (H-D) antigens are important as an immunogenic non-α1,3-galactose (Gal) epitope in pigs with a disrupted α1,3-galactosyltransferase gene. The targeting efficiency of the AO blood genotype was achieved (2.2%) in pig fibroblast cells. A
Jonas Löfling et al.
Virology, 440(1), 89-96 (2013-03-19)
Feline panleukopenia virus (FPV) is a pathogen whose canine-adapted form (canine parvovirus (CPV)) emerged in 1978. These viruses infect by binding host transferrin receptor type-1 (TfR), but also hemagglutinate erythrocytes. We show that hemagglutination involves selective recognition of the non-human

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