N-Glycolylneuraminic AcidA hydroxylated form of sialic acid N-acetylneuraminic acid

N-Glycolylneuraminic Acid (CAS 1113-83-3)

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Synonym: NeuGc
Application: A hydroxylated form of sialic acid N-acetylneuraminic acid
CAS Number: 1113-83-3
Purity: ≥95%
Molecular Weight: 325.3
Molecular Formula: C11H19NO10
* Refer to Certificate of Analysis for lot specific data (including water content).
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N-glycolylneuraminic acid (Neu5Gc) is a hydroxylated form of the generally known sialic acid N-acetylneuraminic acid, Neu5Ac (sc-281055). The compound is biosynthesized by the activity of cytidine monophosphate-N-acetylneuraminate (CMP-Neu5Ac) hydroxylase. Humans do not express Neu5Gc because there is an absence of the hydroxylase acitivity required to convert CMP-Neu5Ac to CMP-Neu5Ac. This is due to a mutation in the gene that occurred after the Homo-Pan divergence. Research shows that the parasite Trypanosoma cruzi contains N-glycoloylneuraminic acid, but is unable to synthesize sialic acids from their precursors.


References

1. Schauer, R., et al. 1983. Hoppe Seylers Z. Physiol. Chem. 364: 1053-1057. PMID: 6354906
2. Shaw, L., et al. 1988. Biol. Chem. Hoppe-Seyler. 369: 477-486. PMID: 3202954
3. Malykh, Y.N., et al. 1998. Glycoconj. J. 15: 885-893. PMID: 10052592
4. Chou, H.H., et al. 1998. Proc. Natl. Acad. Sci. U.S.A. 95: 11751-11756. PMID: 9751737

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (10 mg/ml).
Storage :
Store at -20° C
Melting Point :
188-190° C
Boiling Point :
884.24° C at 760 mmHg (Predicted)
Density :
1.9 g/cm3 (Predicted)
Refractive Index :
n20D 1.65 (Predicted)
pK Values :
pKa: 2.29 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
123802
MDL Number :
MFCD00057551
Beilstein Registry :
1716828
SMILES :
OC[C@@H](O)[C@@H](O)C1OC(O)(CC(O)C1NC(=O)CO)C(O)=O

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Certificate of Analysis

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N-Glycolylneuraminic Acid  Product Citations

See how others have used N-Glycolylneuraminic Acid. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 26295436  Badr, HA. et al. 2015. Biomaterials. 70: 23-36.

PMID: # 9751737  Chou, HH. et al. 1998. Proc. Natl. Acad. Sci. U.S.A. 95: 11751-11756.

Citations 1 to 2 of 2 total
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