Cytidine 5'-monophosphate-N-acetylneuraminic acid

Names

[ Name ]:
Cytidine 5'-monophosphate-N-acetylneuraminic acid

[Synonym ]:
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

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]:

Research Areas >> Metabolic Disease

[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)

MSDS

Click to get detail MSDS

Safety Information

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Glycosylation of immunoglobulin G determines osteoclast differentiation and bone loss.

Nat. Commun. 6 , 6651, (2015)

Immunglobulin G (IgG) sialylation represents a key checkpoint that determines the engagement of pro- or anti-inflammatory Fcγ receptors (FcγR) and the direction of the immune response. Whether IgG sia...

In vitro glycoengineering of IgG1 and its effect on Fc receptor binding and ADCC activity.

PLoS ONE 10 , e0134949, (2015)

The importance and effect of Fc glycosylation of monoclonal antibodies with regard to biological activity is widely discussed and has been investigated in numerous studies. Fc glycosylation of monoclo...

A broadly-protective vaccine against meningococcal disease in sub-Saharan Africa based on generalized modules for membrane antigens (GMMA).

Vaccine 32(23) , 2688-95, (2014)

Neisseria meningitidis causes epidemics of meningitis in sub-Saharan Africa. These have mainly been caused by capsular group A strains, but W and X strains are increasingly contributing to the burden ...