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Merck
CN

C8271

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

≥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

Key Documents

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Product Name

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

InChI key

VFRHSOGUONIUOR-CTFMUGKASA-M

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

biological source

synthetic (organic)

assay

≥85% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

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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

Cytidine-5′-monophospho-N-acetylneuraminic acid (CMP-Sialic acid) is a substrate for sialyltransferases. It is used for the enzymatic sialylation of glycans.
Cytosine 5′-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac) is used as a substrate for Golgi sialyltransferases to form sialic acid and its conjugates.

General description

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

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
0000515252
0000483016
0000483015
0000483015

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Christian Lizak et al.
Scientific reports, 7(1), 5842-5842 (2017-07-21)
Polysialic acid (polySia) is a homopolymeric saccharide that is associated with some neuroinvasive pathogens and is found on selective cell types in their eukaryotic host. The presence of a polySia capsule on these bacterial pathogens helps with resistance to phagocytosis
Yanhong Li et al.
Applied microbiology and biotechnology, 94(4), 887-905 (2012-04-25)
Sialic acids are a family of negatively charged monosaccharides which are commonly presented as the terminal residues in glycans of the glycoconjugates on eukaryotic cell surface or as components of capsular polysaccharides or lipooligosaccharides of some pathogenic bacteria. Due to
Francesca Necchi et al.
PloS one, 12(2), e0172163-e0172163 (2017-02-14)
Serum Bactericidal Activity (SBA) assay is the method of choice to evaluate the complement-mediated functional activity of both infection- and vaccine-induced antibodies. To perform a typical SBA assay, serial dilutions of sera are incubated with target bacterial strains and complement.
Reassembled biosynthetic pathway for a large-scale synthesis of CMP-Neu5Ac
Song J, et al.
Marine drugs, 1(1), 34-45 (2003)
Horasis S Y Leung et al.
Journal of virology, 86(19), 10704-10713 (2012-07-28)
The receptor binding specificity of influenza A virus is one of the major determinants of viral tropism and host specificity. In general, avian viral hemagglutinin prefers to bind to α2,3-linked sialic acid, whereas the human viral hemagglutinin prefers to bind
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