α,β-D-arabinofuranose-5-phosphate disodium salt | 108321-99-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,β-D-arabinofuranose-5-phosphate disodium salt
• 英文别名: disodium D-arabinose 5-phosphate；D-Araf5P
• CAS: 108321-99-9；150713-51-2
• 化学式: C₅H₉O₈P*2Na
• 分子量: 274.075
• InChiKey: LLVQNYOALIWEFG-CTBQCVJASA-L

物化性质

• 熔点：
  113 - 117°C
• 溶解度：
  在水中的溶解度50 mg/mL，澄清，淡黄色

计算性质

• 辛醇/水分配系数(LogP)：
  -6.73
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  142.34
• 氢给体数：
  3.0
• 氢受体数：
  8.0

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 安全说明：
  S22,S24/25,S26,S36

反应信息

• 作为反应物：
  描述：

  α,β-D-arabinofuranose-5-phosphate disodium salt 、 2H-1,2,4-三氮唑-3-甲酰胺 在 purine nucleoside phosphorylase 2-巯基乙醇 、 manganese(ll) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以19%的产率得到1-β-D-arabinofuranosyl-1H-[1,2,4]triazole-3-carboxylic acid amide
  参考文献：
  名称：

  Chemoenzymatic preparation of nucleosides from furanoses

  摘要：

  Chemoenzymatic preparation of ribose, deoxyribose and arabinose 5-phosphates was accomplished. These compounds were tested as starting materials in the enzymatic preparation of natural and modified purine and pyrimidine nucleosides, using an overexpressed Escherichia coli phosphopentomutase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.087
• 作为产物：
  描述：

  [(2R,3R,4S)-4-acetyloxy-5-methoxy-2-(phosphonooxymethyl)oxolan-3-yl] acetate 在 盐酸 作用下， 反应 2.0h， 以0.45 g的产率得到α,β-D-arabinofuranose-5-phosphate disodium salt
  参考文献：
  名称：

  Chemoenzymatic preparation of nucleosides from furanoses

  摘要：

  Chemoenzymatic preparation of ribose, deoxyribose and arabinose 5-phosphates was accomplished. These compounds were tested as starting materials in the enzymatic preparation of natural and modified purine and pyrimidine nucleosides, using an overexpressed Escherichia coli phosphopentomutase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.087

文献信息

• The metal-binding sites of glycose phosphates
  作者：Kathrin Gilg、Tobias Mayer、Natascha Ghaschghaie、Peter Klüfers

  DOI：10.1039/b909431h

  日期：——

  In aqueous solution, the reducing sugar phosphates D-arabinose 5-phosphate, D-ribose 5-phosphate, D-fructose 1,6-bisphosphate, D-fructose 6-phosphate, D-glucose 6-phosphate and D-mannose 6-phosphate provide metal-binding sites at their glycose core on reaction with PdII(en) or MIII(tacn) residues (M = Ga, Co; en = ethylenediamine, tacn = 1,4,7-triazacyclononane). The individual species were detected by one- and two-dimensional NMR spectroscopy. The coordination patterns are related to the metal-binding modes of the respective parent glycoses. In detail, ribo- and arabinofuranose phosphate favour κO1,3 coordination, whereas the ketofuranose core of fructose phosphate and fructose bisphosphate provides the κO2,3 chelator thus maintaining the configuration of the respective major solution anomer. On palladium excess, D-fructose 6-phosphate is metallated twice in a unique κO1,3 : κO2,4 metallation pattern. Dimetallation is also found for the aldohexose phosphates. A mixed glycose-core–phosphate chelation was detected for PdII(en) and MIII(tacn) residues with M = Al, Ga in the pH range just above the physiological pH for the D-fructose 1,6-bisphosphate ligand. The results are discussed in relation to D-fructose-1,6-bisphosphate-metabolism in class-II aldolases.

  在水溶液中，还原糖磷酸盐 D-arabinose 5-磷酸、D-ribose 5-磷酸、D-fructose 1,6-bisphosphate、D-fructose 6-磷酸、D-glucose 6-磷酸和 D-mannose 6-磷酸在与 PdII(en) 或 MIII(tacn) 残基（M = Ga、Co；en=乙二胺，tacn=1,4,7-三氮杂环壬烷）反应时，在其糖核上提供金属结合位点。通过一维和二维核磁共振光谱检测了各个物种。配位模式与各自母糖苷的金属结合模式有关。具体来说，核糖和阿拉伯呋喃糖磷酸有利于κO1,3 配位，而果糖磷酸和果糖双磷酸的酮呋喃糖核心提供了κO2,3 螯合剂，从而保持了各自主要溶液异构体的构型。在钯过量时，D-果糖 6-磷酸会以独特的 κO1,3 : κO2,4 金属化模式发生两次金属化。在醛己糖磷酸盐中也发现了二金属化现象。PdII(en) 和 MIII(tacn) 残基（M = Al、Ga）在略高于 1,6-二磷酸果糖配体生理 pH 值的 pH 范围内检测到一种混合的糖核磷酸盐螯合作用。研究结果与第二类醛缩酶中的 D-果糖-1,6-二磷酸代谢有关。
• Aldolase-catalyzed synthesis of complex C8 and C9 monosaccharides.
  作者：Mark D Bednarski、Herbert J Waldmann、George M Whitesides

  DOI：10.1016/s0040-4039(00)85332-0

  日期：1986.1