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CMP-Sialic Acid (sodium salt)

(Synonyms: CMP-Neu5Ac) 目录号 : GC43287

A nucleotide sugar

CMP-Sialic Acid (sodium salt) Chemical Structure

Cas No.:1007117-62-5

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产品描述

CMP-Sialic acid is a form of the sugar N-acetylneuraminic acid (Neu5Ac) O-linked with the nucleotide cytidine-5’-monophosphate (CMP). In vertebrates, it is biosynthesized within the nucleus from CTP and Neu5Ac by CMP-sialic acid synthetases.[1] Sialyltransferases transfer Neu5Ac from CMP-sialic acid to various acceptor substrates, most commonly at terminal positions of the oligosaccharide component of glycoproteins or glycolipids.[2],[3] Sialic acid-containing glycans at the cell surface play important roles in cell interactions and have roles in infection, inflammation, and cancer.[3],[4],[5]

Reference:
[1]. Münster-Kühnel, A.K., Tiralongo, J., Krapp, S., et al. Structure and function of vertebrate CMP-sialic acid synthetases. Glycobiology 14(10), 43R-51R (2004).
[2]. Tsuji, S. Molecular cloning and functional analysis of sialyltransferases. Journal of Biochemistry 120(1), 1-13 (1996).
[3]. Audry, M., Jeanneau, C., Imberty, A., et al. Current trends in the structure-activity relationships of sialyltransferases. Glycobiology 21(6), 716-726 (2011).
[4]. Hennet, T. From glycosylation disorders back to glycosylation: What have we learned? Biochim.Biophys.Acta. 1792(9), 921-924 (2009).
[5]. Samraj, A.N., Läubli, H., Varki, N., et al. Involvement of a non-human sialic acid in human cancer. Front.Oncol. 4, 33 (2014).

Chemical Properties

Cas No. 1007117-62-5 SDF
别名 CMP-Neu5Ac
化学名 N-acetyl-2-(hydrogen 5'-cytidylate)-β-neuraminic acid, monosodium salt
Canonical SMILES O[C@H]1[C@@H](O)[C@H](N2C=CC(N)=NC2=O)O[C@@H]1COP(O[C@@]3(C(O)=O)C[C@H](O)[C@@H](NC(C)=O)[C@@]([C@H](O)[C@H](O)CO)([H])O3)([O-])=O.[Na+]
分子式 C20H30N4O16P•Na 分子量 636.4
溶解度 10mg/mL in PBS, pH 7.2 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 1.5713 mL 7.8567 mL 15.7134 mL
5 mM 0.3143 mL 1.5713 mL 3.1427 mL
10 mM 0.1571 mL 0.7857 mL 1.5713 mL
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Research Update

Species-specific aggregation factor in sponges. Sialyltransferase associated with aggregation factor

J Biol Chem 1977 Jun 10;252(11):3836-42.PMID:16920doi

The sialyltransferase (= glycoprotein-sialic acid transferase) was studied in the sponge Geodia cydonium, a mesozoan organism. The experiments were performed both in intact cellular and in isolated enzyme systems. It is shown, that desialylated cells show a lower aggregation potency than the controls. During aggregation enzymic sialylation of desialylated sponge cells occurs in the presence of an aggregation factor, which is associated with a high molecular weight particle. The sialylation process is temperature-dependent and can be inhibited by N-ethylmaleimide. Sialylation occurs predominantly at a distinct cell surface component, the aggregation receptor. The sialyltransferase was isolated and purified by the following steps: Sepharose 4B, CM-cellulose, Nonidet treatment, and Sephadex G-100. By this procedure the enzyme was purified 680-fold with a 31% yield. The sialyltransferase is originally associated with the high molecular weight particle also carrying the aggregation factor. In the last step the aggregation factor was separated from the sialyltransferase. The enzyme catalyzes the transfer of sialic acid from CMP-Sialic Acid to the desialylated aggregation receptor. The molecular weight of the sialyltransferase has been determined to be 52,000. Kinetic studies revealed no lag phase and a dependence on enzyme concentration. The purified transferase has a pH optimum of 7.75 and requires 200 mM NaCl for activity. No requirement for Mg2+ or Ca2+ could be observed. The reaction is inhibited by 10 micronM N-ethylmaleimide.