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C8271

Sigma-Aldrich

胞苷-5′-单磷氮乙酰神经氨酸 钠盐

≥85% (HPLC)

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别名:
CMP-NAN, CMP-NANA, CMP-Neu5Ac, CMP-唾液酸
线性分子式:
C20H30N4NaO16P
CAS号:
1007117-62-5
分子量:
636.43
Beilstein:
4224251
MDL编号:
MFCD00151579
PubChem化学物质编号:
24893038
NACRES:
NA.51

生物来源

synthetic (organic)

质量水平

200

检测方案

≥85% (HPLC)

形式

powder

储存温度

−20°C

SMILES字符串

[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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相关类别

一般描述

胞嘧啶5′-单磷酸N-乙酰神经氨酸(CMP-Neu5Ac)是CMP-Neu5Ac合成酶催化CTP和Neu5Ac得到的一种糖核苷酸。

应用

5′-单磷酸胞苷-N-乙酰神经氨酸钠盐已用于：
  • 作为高效阴离子交换色谱-脉冲安培检测法(HPAEC-PAD)的标准品，用于Joubert综合征10型(JBTS10)患者细胞和皮肤成纤维细胞对照的核苷酸糖分析,
  • 作为底物用于G2糖酶促唾液酸化、再唾液酸化检测，
  • 体外唾液酸转移酶检测

生化/生理作用

胞嘧啶5′-单磷酸N-乙酰基神经氨酸(CMP-Neu5Ac)作为高尔基体唾液酸转移酶的底物，用于形成唾液酸及其偶联物。
胞苷-5′-单磷酸酯-N-乙酰基神经氨酸（CMP-唾液酸）是唾液酸转移酶的底物。主要用于多糖的酶促唾液酸化。

制备说明

通过Schauer, R.等人Hoppe Seyler′s Z. Physiol. Chem., 353, 883 （1972）的方法酶促制备。
CMP-NAN是非常酸不稳定的。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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Reassembled biosynthetic pathway for a large-scale synthesis of CMP-Neu5Ac
Song J, et al.
Marine drugs, 1(1), 34-45 (2003)
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
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
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
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
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