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362000

N-Glycolylneuraminic Acid

Name: N-Glycolylneuraminic Acid
Brand: MM

Formed by the action of CMP-Neu5Ac hydroxylase. Humans are devoid of this compound due to a mutation in the human CMP-Neu5Ac hydroxylase gene that occurred after the Homo-Pan divergence.

Synonym(s):

N-Glycolylneuraminic Acid, NeuGc, Neu5Gc

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₉NO₁₀

CAS Number:

1113-83-3

Molecular Weight:

325.27

UNSPSC Code:

12352201

NACRES:

NA.79

MDL number:

MFCD00057551

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Quality Level

100

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze

color

off-white

solubility

water: 10 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

N([C@@H]([C@@H](O)[C@H](O)[C@H](O)CO)[C@@H](O)C(=O)C(=O)O)C(=O)CO

InChI

1S/C10H17NO10/c12-1-3(14)6(16)7(17)5(11-4(15)2-13)8(18)9(19)10(20)21/h3,5-8,12-14,16-18H,1-2H2,(H,11,15)(H,20,21)/t3-,5+,6-,7-,8-/m1/s1

InChI key

YIICUBSXBNCXHW-BOSCHMPASA-N

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Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

General description

Formed by the action of CMP-Neu5Ac hydroxylase. A major component in great ape tissues except brain; however, it is absent in man due to a mutation in the human CMP-Neu5Ac hydroxylase gene that is reported to have occurred after the Homo-Pan divergence.

Other Notes

Chou, H.H., et al. 1998. Proc. Natl. Acad. Sci. USA 95, 11751.
Malykh, Y.N., et al. 1998. Glycoconj. J. 15, 885.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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A mutation in human CMP-sialic acid hydroxylase occurred after the Homo-Pan divergence.

H H Chou et al.

Proceedings of the National Academy of Sciences of the United States of America, 95(20), 11751-11756 (1998-09-30)

Sialic acids are important cell-surface molecules of animals in the deuterostome lineage. Although humans do not express easily detectable amounts of N-glycolylneuraminic acid (Neu5Gc, a hydroxylated form of the common sialic acid N-acetylneuraminic acid, Neu5Ac), it is a major component

The role of CMP-N-acetylneuraminic acid hydroxylase in determining the level of N-glycolylneuraminic acid in porcine tissues.

Y N Malykh et al.

Glycoconjugate journal, 15(9), 885-893 (1999-03-03)

The biosynthesis of the sialic acid N-glycolylneuraminic acid (Neu5Gc) occurs by the action of cytidine monophosphate-N-acetylneuraminate (CMP-Neu5Ac) hydroxylase. Previous investigations on a limited number of tissues suggest that the activity of this enzyme governs the extent of glycoconjugate sialylation with

Global Trade Item Number

SKU	GTIN
362000-10MG	07790788049607

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