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Merck

C8271

Sigma-Aldrich

胞苷-5′-单磷氮乙酰神经氨酸 钠盐

≥85% (HPLC)

别名:

CMP-NAN, CMP-NANA, CMP-Neu5Ac, CMP-唾液酸

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About This Item

线性分子式:
C20H30N4NaO16P
分子量:
636.43
Beilstein:
4224251
MDL號碼:
分類程式碼代碼:
41106305
PubChem物質ID:
NACRES:
NA.51

生物源

synthetic (organic)

品質等級

化驗

≥85% (HPLC)

形狀

powder

儲存溫度

−20°C

SMILES 字串

[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 密鑰

VFRHSOGUONIUOR-CTFMUGKASA-M

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一般說明

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。

應用

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。

準備報告

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。

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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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.
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
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
Fiona Clow et al.
Vaccines, 7(4) (2019-11-27)
Development of a vaccine to limit the impact of antibiotic resistant Neisseria gonorrhoeae is now a global priority. Serum bactericidal antibody (SBA) is a possible indicator of protective immunity to N. gonorrhoeae, but conventional assays measure colony forming units (CFU)
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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The presence of multiple functional groups and stereocenters in complex carbohydrates makes them challenging targets for the organic chemist.

Glycosyltransferases were initially considered to be specific for a single glycosyl donor and acceptor, which led to the one enzyme-one linkage concept. Subsequent observations have refuted the theory of absolute enzymatic specificity by describing the transfer of analogs of some nucleoside mono- or diphosphate sugar donors.

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