1-<3-Aminopropoxy(hydroxy)phosphinyl>-D-myo-inositol 4,5-bisphosphate | 136598-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<3-Aminopropoxy(hydroxy)phosphinyl>-D-myo-inositol 4,5-bisphosphate
• 英文别名: 1-O-(3-aminopropyl-1-phospho)-myo-inositol 4,5-(bis)phosphate；Phosphoric acid 3-amino-propyl ester (1R,2R,3S,4R,5R,6S)-2,3,6-trihydroxy-4,5-bis-phosphonooxy-cyclohexyl ester；3-aminopropyl [(1R,2R,3S,4R,5R,6S)-2,3,6-trihydroxy-4,5-diphosphonooxycyclohexyl] hydrogen phosphate
• CAS: 136598-00-0
• 化学式: C₉H₂₂NO₁₅P₃
• 分子量: 477.193
• InChiKey: WLNPFFJULRQOST-JZHWRPJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  276
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-叠氮基水杨酸 N-羟基琥珀酰亚胺酯 、 1-<3-Aminopropoxy(hydroxy)phosphinyl>-D-myo-inositol 4,5-bisphosphate 在 三乙基碳酸氢铵缓冲液 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以13.3 mg的产率得到1-O--myo-inositol-4,5-bisphosphate
  参考文献：
  名称：

  Tethered IP3. Synthesis and biochemical applications of the 1-O-(3-aminopropyl) ester of inositol (1,4,5)-trisphosphate

  摘要：

  A phosphodiester analogue of the second messenger Ins(1,4,5)P3 has been synthesized and used to prepare a novel photoaffinity label and a selective bioaffinity matrix. A selectively protected inositol precursor was first converted by phosphite ester chemistry to an N-protected 1-O-(3-aminopropyl-1-phospho)-DL-myo-inositol and then phosphorylated to give a fully benzylated IP3 derivative. Hydrogenolysis gives the title compound, which was converted to a photolabile analogue and was immobilized on a polymeric resin. The analogues all competed with [H-3]Ins(1,4,5)P3 for binding to purified IP3 receptors from rat brain. Reconstituted receptor liposomes showed calcium release when stimulated by the tethered IP3 materials. None of the new materials were substrates for the 5-phosphatase or the 3-kinase that normally act on Ins(1,4,5)P3.

  DOI：

  10.1021/ja00005a055
• 作为产物：
  描述：

  1-<3-Aminopropoxy(hydroxy)phosphinyl>-2,3,6-tri-O-benzoyl-D-myo-inositol 4,5-bisphosphate 在 ammonium hydroxide 作用下， 反应 18.0h， 生成 1-<3-Aminopropoxy(hydroxy)phosphinyl>-D-myo-inositol 4,5-bisphosphate
  参考文献：
  名称：

  Syntheses of d-myo-inositol 1,4,5-trisphosphate affinity ligands

  摘要：

  A mixture of 2,3,6-tri-O-benzoyl-4,5-di-O-benzyl-D-myo-inositol and 1,3,6-tri-O-benzoyl-4,5-di-O-benzyl-D-myo-inositol, obtained during our synthesis of D-myo-inositol 1,4,5-trisphosphate [C.E. Ballou and W. Tegge, Proc. Natl. Acad. Sci. U.S.A., 86 (1989) 94-98], was separated after tetrahydropyranylation of the free hydroxyl group in each 2,3,6-Tri-O-benzoyl-4,5-di-O-benzyl-1-O-(tetrahydro-2-pyranyl)-D-myo-inositol was debenzylated and the two free hydroxyl groups were phosphorylated by a dinebzyl phosphoramidite procedure. The tetrahydropyranyl group was then removed, and phosphorylation at position 1 with benzyl 3-(benzyloxycarbonylamino)propyl di-N-isopropylphosphoramidite, followed by oxidation and deprotection, provided 1-[3-aminopropoxy(hydroxy)phosphinyl]-D-myo-inositol 4,5-bis-phosphate. This compound was coupled to activated agarose to prepare an affinity matrix for the isolation of D-myo-inositol 1,4,5-trisphosphate-binding proteins, and it was coupled to 4-azido-2-hydroxybenzoic acid to give a product that was labeled with I-125 to prepare a photoactivity derivatizing reagent. The new derivatives retain significant biological activity as assessed by their ability to stimulate the release of stored Ca2+ from the endoplasmic reticulum of permeabilized rat basophilic leukemia cells.

  DOI：

  10.1016/s0008-6215(00)90513-5

文献信息

• Synthesis and evaluation of 1-position-modified inositol 1,4,5-trisphosphate analogs
  作者：Takanari Inoue、Kazuya Kikuchi、Kenzo Hirose、Masamitsu Iino、Tetsuo Nagano

  DOI：10.1016/s0960-894x(99)00256-5

  日期：1999.6

  IP3 analogs were synthesized by the modification of phosphate at the 1-position, and their affinity for the IP3 receptor was analyzed by means of surface plasmon resonance measurements. Our results suggest that a hydrophobic and charged moiety linked to this position enhances the affinity for the IP3 receptor. (C) 1999 Elsevier Science Ltd. All rights reserved.