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C8271

Sigma-Aldrich

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

≥85% (HPLC)

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
Beilstein/REAXYS Number:
4224251
MDL number:
MFCD00151579
UNSPSC Code:
41106305
PubChem Substance ID:
24893038
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥85% (HPLC)

form

powder

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

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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

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.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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.
Magali Audry et al.
Glycobiology, 21(6), 716-726 (2010-11-26)
Sialyltransferases (STs) represent an important group of enzymes that transfer N-acetylneuraminic acid (Neu5Ac) from cytidine monophosphate-Neu5Ac to various acceptor substrates. In higher animals, sialylated oligosaccharide structures play crucial roles in many biological processes but also in diseases, notably in microbial
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
Gillian Dekkers et al.
Frontiers in immunology, 8, 877-877 (2017-08-22)
Glycosylation of the immunoglobulin G (IgG)-Fc tail is required for binding to Fc-gamma receptors (FcγRs) and complement-component C1q. A variety of IgG1-glycoforms is detected in human sera. Several groups have found global or antigen-specific skewing of IgG glycosylation, for example
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