N-Cbz-amino-1-propanol | 65935-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Cbz-amino-1-propanol
• 英文别名: Phenyl (3-hydroxypropyl)carbamate；phenyl N-(3-hydroxypropyl)carbamate
• CAS: 65935-02-6
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: ZXBWMMVKIGCQMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Cbz-amino-1-propanol 、 苄基-N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 以70%的产率得到(benzyloxy)<(N-Cbz-3-aminopropyl)oxy>(N,N-diisopropylamino)phosphine
  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

文献信息

• Tethered IP3. Synthesis and biochemical applications of the 1-O-(3-aminopropyl) ester of inositol (1,4,5)-trisphosphate
  作者：Glenn D. Prestwich、James F. Marecek、Robert J. Mourey、Anne B. Theibert、Christopher D. Ferris、Sonye K. Danoff、Solomon H. Snyder

  DOI：10.1021/ja00005a055

  日期：1991.2

  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.