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C8271

Cytidine-5′-monophospho-N-acetylneuraminic acid sodium salt

Name: Cytidine-5&#8242;-monophospho-N-acetylneuraminic acid sodium salt
Brand: SIGMA

≥85% (HPLC), synthetic (organic), powder

Synonym(s):

CMP-NAN, CMP-NANA, CMP-Neu5Ac, CMP-Sialic acid

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About This Item

Linear Formula:

C₂₀H₃₀N₄NaO₁₆P

CAS Number:

1007117-62-5

Molecular Weight:

636.43

NACRES:

NA.51

PubChem Substance ID:

24893038

UNSPSC Code:

41106305

MDL number:

MFCD00151579

Beilstein/REAXYS Number:

4224251

Assay:

≥85% (HPLC)

Biological source:

synthetic (organic)

Form:

powder

Solubility:

water: 50 mg/mL, clear, colorless

Storage temp.:

−20°C

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Properties

Product Name

Cytidine-5′-monophospho-N-acetylneuraminic acid sodium salt, ≥85% (HPLC)

biological source

synthetic (organic)

Quality Level

200

assay

≥85% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na+].CC(=O)N[C@@H]1[C@@H](O)C[C@@](O[C@@H]1[C@H](O)[C@H](O)CO)(OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(N)=NC3=O)C(O)=O

InChI

1S/C20H31N4O16P.Na/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34;/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34);/q;+1/p-1/t8-,9+,10+,12+,13+,14+,15+,16?,17+,20+;/m0./s1

InChI key

VFRHSOGUONIUOR-CTFMUGKASA-M

Description

General description

Cytosine 5′-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac) is a sugar-nucleotide produced by CMP-Neu5Ac synthetase from CTP and Neu5Ac.

Application

Cytidine-5′-monophospho-N-acetylneuraminic acid sodium salt has been used:

as a standard in high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) for nucleotide sugar analysis in Joubert syndrome type 10 (JBTS10) patient cells and control skin fibroblasts,
As a substrate for the enzymatic sialylation of G2 glycoforms, resialylation assay,
in in-vitro sialyltransferase assay

Biochem/physiol Actions

Cytosine 5′-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac) is used as a substrate for Golgi sialyltransferases to form sialic acid and its conjugates.

Cytidine-5′-monophospho-N-acetylneuraminic acid (CMP-Sialic acid) is a substrate for sialyltransferases. It is used for the enzymatic sialylation of glycans.

Preparation Note

Enzymatically prepared by the method of Schauer, R., et al., Hoppe Seyler′s Z. Physiol. Chem., 353, 883 (1972).
CMP-NAN is very acid-labile.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000515252

0000483016

0000483015

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