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Merck

C8271

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

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

Sinónimos:

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

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1 MG

MXP 2,164.00

5 MG

MXP 8,415.00

25 MG

MXP 45,589.00

MXP 2,164.00

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Fórmula lineal:
C20H30N4NaO16P
Número CAS:
1007117-62-5
Peso molecular:
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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Nombre del producto

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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Este artículo
C963030290D0627
Cytidine-5′-monophospho-N-acetylneuraminic acid sodium salt ≥85% (HPLC)

Sigma-Aldrich

C8271

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

Cytidine 2′:3′-cyclic monophosphate monosodium salt ≥95% (HPLC)

Sigma-Aldrich

C9630

Cytidine 2′:3′-cyclic monophosphate monosodium salt

Cytidine 5′-diphosphocholine sodium salt hydrate ≥99.0% (HPLC)

Sigma-Aldrich

30290

Cytidine 5′-diphosphocholine sodium salt hydrate

N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt ≥96% (HPLC), powder

Sigma-Aldrich

D0627

N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt

biological source

synthetic (organic)

biological source

synthetic

biological source

synthetic

biological source

synthetic (organic)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

form

powder

form

powder

form

powder

form

powder

assay

≥85% (HPLC)

assay

≥95% (HPLC)

assay

≥99.0% (HPLC)

assay

≥96% (HPLC)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

General description

Cytosine 5′-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac) is a sugar-nucleotide produced by CMP-Neu5Ac synthetase from CTP and Neu5Ac.[1]

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[2],
  • As a substrate for the enzymatic sialylation of G2 glycoforms[3], resialylation assay[4][5][6],
  • in in-vitro sialyltransferase assay[7]

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.[8][1]

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000483016
0000483015
0000483015
0000483016
0000481083

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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.
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
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
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
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