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
• 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

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[1],
• As a substrate for the enzymatic sialylation of G2 glycoforms[2], resialylation assay[3][4][5],
• in in-vitro sialyltransferase assay[6]

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.[7]

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable