Cytidine 5'-monophosphate-N-acetylneuraminic acid

Modify Date: 2024-01-02 14:00:31

Cytidine 5'-monophosphate-N-acetylneuraminic acid Structure
Cytidine 5'-monophosphate-N-acetylneuraminic acid structure
Common Name Cytidine 5'-monophosphate-N-acetylneuraminic acid
CAS Number 3063-71-6 Molecular Weight 636.433
Density 2.02g/cm3 Boiling Point N/A
Molecular Formula C20H30N4NaO16P Melting Point N/A
MSDS USA Flash Point N/A

 Use of Cytidine 5'-monophosphate-N-acetylneuraminic acid


CMP-Sialic acid (CMP-Neu5Ac) is an allosteric inhibitor of UDP-GlcNAc 2-epimerase. CMP-Sialic acid provides a substrate for Golgi sialyltransferases. CMP-Sialic acid is an important sugar nucleotide for biosynthesis of sialic acid and its conjugates[1].

 Names

Name CMP-N-acetyl-β-neuraminic acid
Synonym More Synonyms

  Biological Activity

Description CMP-Sialic acid (CMP-Neu5Ac) is an allosteric inhibitor of UDP-GlcNAc 2-epimerase. CMP-Sialic acid provides a substrate for Golgi sialyltransferases. CMP-Sialic acid is an important sugar nucleotide for biosynthesis of sialic acid and its conjugates[1].
Related Catalog
Target

Human Endogenous Metabolite

In Vitro CMP-Sialic acid (22.5 μM, 45 min) 可用作 CMAH 底物来检测血小板裂解物中 Neu5Gc 的形成[1]。
References

[1]. Münster AK, et al. Mammalian cytidine 5'-monophosphate N-acetylneuraminic acid synthetase: a nuclear protein with evolutionarily conserved structural motifs. Proc Natl Acad Sci U S A. 1998 Aug 4;95(16):9140-5.  

[2]. Jing Song, et al. Reassembled Biosynthetic Pathway for a Large-scale Synthesis of CMP-Neu5Ac. Mar Drugs. 2003 Dec; 1(4): 34-45.

[3]. Mercado CP, et al. A serotonin-induced N-glycan switch regulates platelet aggregation. Sci Rep. 2013 Sep 30;3:2795.  

 Chemical & Physical Properties

Density 2.02g/cm3
Molecular Formula C20H30N4NaO16P
Molecular Weight 636.433
Exact Mass 636.129211
PSA 335.55000
Index of Refraction 1.737
Water Solubility Freely soluble (220 g/L) (25 ºC)

 Safety Information

Risk Phrases 36/37/38
Safety Phrases 26
RIDADR NONH for all modes of transport
WGK Germany 3

 Synthetic Route

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 Synonyms

CMP-b-D-Sialic Acid,DisodiumSalt
CMP-NAN,CMP-NANA,CMP-NeuAc,CMP-Sialic acid
CMP-Sia
Cytidine-5'-monophospho-N-acetylneuraminic acid disodium salt
CMP-N-acetyl-beta-neuraminic acid
Cytidine monophosphate n-acetylneuraminic acid
cytidine 5-monophospho-N-*acetylneuraminic acid
Sodium (2R,4S,5R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(4-amino-2-oxo-1(2H)-pyrimidinyl)-3,4-dihydroxytetrahydro-2-furanyl]methyl phosphate
CYTIDINE 5'-MONOPHOSPHO-N-
cytidine-5'-monophospho-N-acetyl-D-neuraminic acid
cytidine 5'-monophospho-N-acetylneuraminic acid,sodium
cmp-nan
CMP-N-Acetylneuraminic Acid
CMP-sialic acid
CMP-Sialic Acid, Monosodium Salt
Cytidine 5'-monophosphate-N-acetylneuraminic acid
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