1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-ulose 5-dibenzylphosphate | 270076-03-4

• 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: 1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-ulose 5-dibenzylphosphate
• 英文别名: [(3aR,5R,6aS)-2,2-dimethyl-6-oxo-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl dibenzyl phosphate
• CAS: 270076-03-4
• 化学式: C₂₂H₂₅O₈P
• 分子量: 448.409
• InChiKey: AXOVBHXXXHJPIA-HMXCVIKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-ulose 5-dibenzylphosphate 在 三氟甲磺酸 sodium tetrahydroborate 、 sodium periodate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 7.0h， 生成 2-O-benzyl-2-C-methyl-D-erythritol 4-dibenzylphosphate
  参考文献：
  名称：

  对映体纯2 - C-甲基-d-赤藓糖醇4-磷酸的化学合成，是类异戊二烯生物合成的甲羟戊酸非依赖性途径中的关键中间体

  摘要：

  光学纯的2 - C-甲基-d-赤藓糖醇4-磷酸酯是类戊二烯类生物合成的甲羟戊酸非依赖性途径的关键中间体，可以方便地由1,2 - O-异亚丙基-α-d-木呋喃糖合成，包括对该基板进行无线电标记。

  DOI：

  10.1016/s0040-4020(00)00065-x
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 重铬酸吡啶 、 molecular sieve 、 溶剂黄146 作用下， 以 吡啶 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-ulose 5-dibenzylphosphate
  参考文献：
  名称：

  对映体纯2 - C-甲基-d-赤藓糖醇4-磷酸的化学合成，是类异戊二烯生物合成的甲羟戊酸非依赖性途径中的关键中间体

  摘要：

  光学纯的2 - C-甲基-d-赤藓糖醇4-磷酸酯是类戊二烯类生物合成的甲羟戊酸非依赖性途径的关键中间体，可以方便地由1,2 - O-异亚丙基-α-d-木呋喃糖合成，包括对该基板进行无线电标记。

  DOI：

  10.1016/s0040-4020(00)00065-x

文献信息

• Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-d-erythritol: a substrate for IspE
  作者：Prabagaran Narayanasamy、Hyungjin Eoh、Dean C. Crick

  DOI：10.1016/j.tetlet.2008.05.074

  日期：2008.7

  Enantiomerically pure 2-C-methyl-D-erythritol 4-phosphate 1 (MEP) is synthesized from 1,2-O-isopropylidene-alpha-D-xylofuranose via facile benzylation in good yield. Subsequently, 1 is used for enzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2 (CDP-ME) using 4-diphosphocytidyl-2-Cmethyl-D-erythritol synthase (IspD). The chemoenzymatically synthesized 2 can be used as substrate for assay of IspE and for high throughput screening to identify 1spE inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.
• Expression and Characterization of Soluble 4-Diphosphocytidyl-2-C-methyl-D-erythritol Kinase from Bacterial Pathogens
  作者：Hyungjin Eoh、Prabagaran Narayanasamy、Amanda C. Brown、Tanya Parish、Patrick J. Brennan、Dean C. Crick

  DOI：10.1016/j.chembiol.2009.10.014

  日期：2009.12

  Many bacterial pathogens utilize the 2-C-methyl-D-erythritol 4-phosphate pathway for biosynthesizing isoprenoid precursors, a pathway that is vital for bacterial survival and absent from human cells, providing a potential source of drug targets. However, the characterization of 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDP-ME) kinase (IspE) has been hindered due to a lack of enantiopure CDP-ME and difficulty in obtaining pure IspE. Here, enantiopure CDP-ME was chemically synthesized and recombinant IspE from bacterial pathogens were purified and characterized. Although gene disruption was not possible in Mycobacterium tuberculosis, IspE is essential in Mycobacterium smegmatis. The biochemical and kinetic characteristics of IspE provide the basis for development of a high throughput screen and structural characterization.
• Chemical Synthesis of Enantiopure 2-C-Methyl-d-Erythritol 4-Phosphate, the Key Intermediate in the Mevalonate-Independent Pathway for Isoprenoid Biosynthesis
  作者：Jean-François Hoeffler、C Pale-Grosdemange、Michel Rohmer

  DOI：10.1016/s0040-4020(00)00065-x

  日期：2000.3

  Optically pure 2-C-methyl-d-erythritol 4-phosphate, a key intermediate in the mevalonate-independent route for isoprenoid biosynthesis, is conveniently synthesized from 1,2-O-isopropylidene-α-d-xylofuranose, including the possibility of radiolabeling of this substrate.

  光学纯的2 - C-甲基-d-赤藓糖醇4-磷酸酯是类戊二烯类生物合成的甲羟戊酸非依赖性途径的关键中间体，可以方便地由1,2 - O-异亚丙基-α-d-木呋喃糖合成，包括对该基板进行无线电标记。