inositol 1,2-cyclic phosphate | 43119-57-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: inositol 1,2-cyclic phosphate
• 英文别名: 1D-myo-inositol 1,2-cyclic phosphate；(3aR,4R,5S,6S,7R,7aS)-2-hydroxy-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]dioxaphosphole-4,5,6,7-tetrol
• CAS: 43119-57-9
• 化学式: C₆H₁₁O₈P
• 分子量: 242.122
• InChiKey: SXHMVNXROAUURW-FTYOSCRSSA-N

物化性质

• 沸点：
  436.8±55.0 °C(Predicted)
• 密度：
  2.00±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  inositol 1,2-cyclic phosphate 以 水 为溶剂， 生成 (+/-)-myo-Inositol-1-phosphate
  参考文献：
  名称：

  Zhiwen, Guan; Bruzik, Karol S., Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 111, p. 69

  摘要：

  DOI：
• 作为产物：
  描述：

  Phosphoric acid 2,2-difluoro-dodecyl ester (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl ester 在 乙二胺四乙酸 、 MOPS buffer 、 wild-type phosphatidylinositol-specific phospholipase C 作用下， 以 重水 为溶剂， 生成 inositol 1,2-cyclic phosphate
  参考文献：
  名称：

  Brønsted型LFER在磷脂酶C机制研究中的应用†

  摘要：

  磷脂酰肌醇特异性磷脂酶裂解磷脂酰肌醇的磷酸二酯键，形成肌醇 1,2-环磷酸酯和甘油二酯。该酶还接受各种烷基和芳基肌醇磷酸酯作为底物，使其成为通过探测线性自由能关系 (LFER) 研究磷酰基转移机制的合适模型酶。在这项工作中，我们对 Brønsted 型关系 (log k = beta(lg) pK(a) + C) 进行了研究，以比较酶促和非酶促反应的机制，确认早先提出的机制，并进一步评估疏水性的作用在离去基团中作为一般的酸促进因子。观察到两种非酶促 (beta(lg) = -0.65 到 -0) 的高负 Brønsted 系数。73) 和芳基和非疏水性烷基肌醇磷酸酯的酶促裂解 (beta(lg) = -0.58) 表明这些反应仅涉及弱的一般酸催化。相比之下，疏水性烷基肌醇磷酸酯的酶促裂解表现出较低的负布朗斯台德系数（β（lg）= -0.12），表明离去基团上有少量负电荷和有效的一般酸催化。

  DOI：

  10.1021/ja029362s

文献信息

• Recherches dans la série des cyclitols XXVI. Obtention d'inositol-phosphodiesters cycliques et transposition d'esters inositol-monophosphoriques
  作者：Th. Posternak

  DOI：10.1002/hlca.19580410644

  日期：——

  La formation de phosphodiesters-1,2 cycliques a été observée à partir de l'acide scyllitol-phosphorique et de l'acide ms-inositol-2-phosphorique; la substance formée à partir de ce dernier a été préparée comme sel de baryum analytiquement pur. Par traitement acide ou alcalin ménagé, elle fournit deux produits, vraisemblablement les acides ms-inositol-2- et -1(3)-phosphoriques, le dernier étant en quantité

  形成磷酸二酯-1，2，2，3，5-环己基鞘氨醇-磷酸酯的观察和发现-甲基肌醇-2-磷酸酯。在巴雷姆分析中使用的基本物质和安全证书。酸度或碱性磷酸酶的特征，酸性产物ms-inositol-2- et -1（3）-磷光体的可重组性，定量的抗微生物剂。混合糖类的合成品和类似品的混合物大豆和肌醇磷酸酯类产品的代用组合物酸性和磷酸二乙酯-磷酸肌醇类的特征-O-乙酰基-1,3,4,5,6-O-二苯基磷酰基-2-ms-肌醇 水解碱性蛋白酶物质导管 按比例倒置作曲。肌醇中的磷酸酯类和肌醇的磷酸酯类，以及可能的磷酸化肌醇水解的可能的替代品。
• Synthesis and Kinetic Evaluation of Inhibitors of the Phosphatidylinositol-Specific Phospholipase C from <i>Bacillus cereus</i>
  作者：Stephen F. Martin、Allan S. Wagman

  DOI：10.1021/jo960850q

  日期：1996.11.15

  Substrate analogues of phosphatidylinositol (1) were synthesized and evaluated as potential inhibitors of the bacterial phosphatidylinositol-specific phospholipase C (PI-PLC) from Bacillus cereus. The chiral analogues of the water-soluble phospholipid substrate 5 were designed to probe the effects of varying the inositol C-2 hydroxyl group, which is generally believed to serve as the nucleophile in

  合成了磷脂酰肌醇（1）的底物类似物，并评估为蜡状芽孢杆菌的细菌磷脂酰肌醇特异性磷脂酶C（PI-PLC）的潜在抑制剂。水溶性磷脂底物5的手性类似物被设计成探测改变肌醇C-2羟基的作用，通常认为它通过PI-PLC在磷脂酰肌醇水解的第一步中用作亲核试剂。在类似物6-9中，磷脂酰肌醇衍生物的肌醇环上的C-2羟基以几种方式被合理地改变。肌醇环C-2处的立体化学颠倒导致了scyllo衍生物6。肌醇C-2羟基被氟取代，以产生烷基-氟代肌醇7，氢原子被取代以提供2-脱氧化合物8。C-2羟基被O-甲基化以制备甲氧基衍生物9. C-2处的天然肌醇构型保留在不可水解的二硫代磷酸酯类似物10中。然后使用D-肌醇1-（4-硝基苯基）在连续测定法中分析这些类似物对PI-PLC的抑制作用（25）作为发色底物。确定了每种磷脂酰肌醇衍生物的动力学参数，发现它们是具有K（i）的竞争性抑制剂，如下：6,0.2mM; 10，0.6毫米;
• Synthesis of a new fluorogenic substrate for the assay of phosphoinositide-specific phospholipase C
  作者：Aleksey V. rukavishnikov、Miles P. Smith、G. Bruce Birrell、John F.W. Keana、O. Hayes Griffith

  DOI：10.1016/s0040-4039(98)01429-4

  日期：1998.9

  The synthesis of a fluorescein-derived fluorogenic substrate, D,L-myo-inositol l-([6′-hexyloxy-3-oxo]spiro[isobenzofuran-1(3H),9′-[9H]xanthen]-3′-yl hydrogen phosphate) sodium salt 9, for assay of activity of phosphatidylinositide-specific phospholipase C (PI-PLC), is described. This substrate is shown to be a sensitive substrate for bacterial PI-PLC in a continuous, non-radioactive assay.

  荧光素衍生的荧光底物，d，L-的合成肌肉（[6'-己氧基-3-氧代]螺-肌醇升[异苯并呋喃-1（3 ħ），9' - [9 ħ ]呫吨] -描述了用于测定磷脂酰肌醇特异性磷脂酶C（PI-PLC）的活性的3'-磷酸磷酸氢钠盐9。在连续的非放射性测定中，该底物显示为细菌PI-PLC的敏感底物。
• Synthesis of Inositol Phosphodiesters by Phospholipase C-Catalyzed Transesterification
  作者：Karol S. Bruzik、Zhiwen Guan、Suzette Riddle、Ming-Daw Tsai

  DOI：10.1021/ja9616084

  日期：1996.1.1

  Transesterification of primary alcohols with inositol 1,2-cyclic phosphate (IcP) in the presence of phosphatidylinositol-specific phospholipase C (PI-PLC) resulted in the formation of O-alkyl inositol 1-phosphates. The starting IcP was obtained in a single step by PI-PLC catalyzed cleavage of phosphatidylinositol from the soybean phospholipid. The transesterification reaction was performed with a series of 20 structurally diverse hydroxyl compounds, ranging in the structural complexity from methanol to the serine-containing Ser-Tyr-Ser-Met tetrapeptide, to give the corresponding phosphodiesters with 20-80% yields, depending mainly on the solubility of alcohols in water. The rates of transesterifications, and of the competing hydrolysis of IcP to inositol 1-phosphate (IP), were relatively insensitive to the alcohol structure. With polyhydroxyl compounds such as glycerol and hexitols, the enzyme displayed complete preference toward formation of the inositol phosphate derivatives of the primary hydroxyl groups. On the other hand, PI-PLC did not discriminate between primary hydroxyl groups in different environments and showed low stereoselectivity with racemic alcohols featuring a chiral center at the beta-position, The O-alkyl inositol phosphates formed were readily separable from the hydrolytic product, IP, by the anion-exchange chromatography, and were fully characterized by means of H-1 and P-31 NMR and electrospray MS. Our results provide a new, simple, and efficient two-step synthetic route to substituted O-alkyl inositol phosphates from inexpensive starting materials. The reported reaction was successfully applied to synthesis of complex inositol phosphate derivatives, as illustrated by inositol phosphoesters of mono- and oligosaccharides, nucleosides and peptides. The synthetic usefulness of this reaction, however, is not limited to the examples shown. Because transesterification activity of phospholipase C has not been reported before, its mechanism is discussed in a broad context of mechanisms of phosphoesterases.
• Studies on myo-Inositol Phosphates of Natural Origin
  作者：Frances Lane Pizer、Clinton E. Ballou

  DOI：10.1021/ja01513a040

  日期：1959.3