D-myo-inositol 1,2,3,4-tetrakisphosphate | 114418-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-myo-inositol 1,2,3,4-tetrakisphosphate
• 英文别名: [(1S,2R,3R,4S,5S,6R)-2,3-dihydroxy-4,5,6-triphosphonooxycyclohexyl] dihydrogen phosphate
• CAS: 114418-90-5
• 化学式: C₆H₁₆O₁₈P₄
• 分子量: 500.077
• InChiKey: MRVYFOANPDTYBY-JIGFOQOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  308
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  D-myo-inositol 1,2,3,4-tetrakisphosphate 在 InsP₄-phosphohydrolase 作用下， 以 水 为溶剂， 以99%的产率得到Inositol 1,2,3-triphosphate
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x
• 作为产物：
  描述：

  (1S,2S,3S,4S)-anti-benzene dioxide 在 palladium on activated charcoal 吡啶 、 四氮唑 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 氢气 、 间氯过氧苯甲酸 作用下， 生成 D-myo-inositol 1,2,3,4-tetrakisphosphate
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x

文献信息

• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 1): Via Symmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400911

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  描述了用于制备肌醇磷酸酯的实用路线。通过酶促拆分二乙酰氧基硬糖醇关键中间体，可以从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可以通过破坏 conduritol B 衍生物的 C2 对称性来获得。通过将先前报道的对称方法与这种新的非对称方法相结合，可以合成多种肌醇磷酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Process for the preparation of myoinositol derivatives
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0262227A1

  公开（公告）日：1988-04-06

  Myoinositol phosphates and salts thereof represented by general formula (I) and process for their preparation. The myoinositol derivatives are prepared by reacting a phosphorylating agent with a myoinositol derivative wherein sites other than those to be substituted by phosphate residues are substituted by a substituent capable of being eliminated by catalytic reduction, and subjecting the product to catalytic reduction.

  由通式(I)表示的肌醇磷酸盐及其盐类以及它们的制备方法。肌醇衍生物的制备方法是将磷酸化剂与肌醇衍生物反应，其中磷酸残基取代的位点以外的位点被能够通过催化还原消除的取代基取代，然后将产物进行催化还原。
• Divergent Syntheses of All Possible Optically Active Regioisomers of <i>m</i><i>yo</i>-Inositol Tris- and Tetrakisphosphates
  作者：Sung-Kee Chung、Yong-Uk Kwon、Jung-Han Shin、Young-Tae Chang、Changgook Lee、Boo-Gyo Shin、Kyung-Cheol Kim、Mahn-Joo Kim

  DOI：10.1021/jo0257694

  日期：2002.8.1

  Since the discovery Of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz(3)s and IBz(2)s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositoI and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz(3) and six enantiomeric pairs of IBz(2), respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.
• US4952717A
  申请人：——

  公开号：US4952717A

  公开（公告）日：1990-08-28
• US5292913A
  申请人：——

  公开号：US5292913A

  公开（公告）日：1994-03-08