1-O-<3-Formylaminopropoxy(hydroxy)phosphinyl>-D-myo-inositol 4,5-bisphosphate | 143366-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-<3-Formylaminopropoxy(hydroxy)phosphinyl>-D-myo-inositol 4,5-bisphosphate
• CAS: 143366-63-6
• 化学式: C₁₀H₂₂NO₁₆P₃
• 分子量: 505.203
• InChiKey: YYSPVCFMYDUIAA-SWKORFGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.32
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  279.07
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  1-<3-Aminopropoxy(hydroxy)phosphinyl>-2,3,6-tri-O-benzoyl-D-myo-inositol 4,5-bisphosphate 在 甲醇 、 sodium hydroxide 作用下， 反应 90.0h， 生成 1-O-<3-Formylaminopropoxy(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