(2R,3S)-2,3,4-三羟基-3-甲基丁基磷酸二氢酯 | 206440-72-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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
• 中文名称: (2R,3S)-2,3,4-三羟基-3-甲基丁基磷酸二氢酯
• 中文别名: 2-C-甲基-D-赤藓糖醇-4-磷酸酯；甲基-D-赤藓醇磷酸盐
• 英文名称: 2-C-methyl-D-erythritol 4-phosphoric acid
• 英文别名: 2-C-methyl-D-erythritol 4-phosphate；2-C-methyl-D-erythritol-4-phosphate；2C-methyl-D-erythritol 4-phosphate；methylerythritol phosphate；MEP；Methyl-D-erythritol Phosphate；[(2R,3S)-2,3,4-trihydroxy-3-methylbutyl] dihydrogen phosphate
• CAS: 206440-72-4
• 化学式: C₅H₁₃O₇P
• 分子量: 216.128
• InChiKey: XMWHRVNVKDKBRG-UHNVWZDZSA-N

物化性质

• 沸点：
  530.7±60.0 °C(Predicted)
• 密度：
  1.668±0.06 g/cm3(Predicted)
• 溶解度：
  溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 储存条件：
  -20°C，密封保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  5'-胞苷酸 、 (2R,3S)-2,3,4-三羟基-3-甲基丁基磷酸二氢酯 在 Streptomyces coelicolor MEP ciytidylyl transferase YgbP 作用下， 以 水 为溶剂， 生成 氨基嘧啶酮-4-二磷酸二胺-2-C-甲基-D-赤藓糖醇
  参考文献：
  名称：

  Molecular cloning, expression and characterization of the first three genes in the mevalonate-independent isoprenoid pathway in Streptomyces coelicolor

  摘要：

  The mevalonate-independent biosynthetic pathway to isopentenyl diphosphate and dimethylallyl diphosphate, the universal precursors to the isoprenoids, operates in eubacteria, including Escherichia coli, in algae, and in the plastids of higher plants. A search of the Sanger Centre Streptomyces coelicolor genome database revealed open reading frames with ca. 40-50% identity at the deduced amino acid level to the first three E. coli enzymes of this pathway, corresponding to deoxyxylulose phosphate synthase, deoxyxylulose phosphate reductoisomerase and 2-C-methyl erythritol 4-phosphate cytidylyltransferase. The S. coelicolor genes have been cloned and expressed in E. coli, and the recombinant proteins characterized physically and kinetically. The presence of the corresponding enzyme activities in extracts of S. coelicolor CH999 further supports the operation of the mevalonate-independent pathway in this organism. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00050-5
• 作为产物：
  描述：

  DXP 钠盐 在 1-deoxy-D-xylulose 5-phosphate reductoisomerase,Tris-HCl 、 三羟甲基氨基甲烷盐酸盐 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 作用下， 反应 0.5h， 生成 (2R,3S)-2,3,4-三羟基-3-甲基丁基磷酸二氢酯
  参考文献：
  名称：

  Direct formation of 2-C-methyl-d-erythritol 4-phosphate from 1-deoxy-d-xylulose 5-phosphate by 1-deoxy-d-xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate

  摘要：

  1-Deoxy-D-xylulose 5-phosphate is biotransformed to 2-C-methyl-D-erythritol 4-phosphate in a single step in die presence of NADPH by a new recombinant enzyme named I-deoxy-D-xylulose 5-phosphate reductoisomerase purified from Escherichia coli. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00802-8

文献信息

• A convenient synthesis of 2-C-methyl-d-erythritol 4-phosphate and isotopomers of its precursor
  作者：Alexandros E. Koumbis、Stefanos S. Kotoulas、John K. Gallos

  DOI：10.1016/j.tet.2006.12.078

  日期：2007.3

  A new synthetic approach toward 2-C-methyl-d-erythritol 4-phosphate (MEP), a key intermediate in the mevalonate-independent biosynthetic pathway for isoprenoids, and deuterated analogues of its precursor, 2-C-methyl-d-erythritol acetonide, is described. This procedure uses 2-C-methyl-d-erythrose acetonide as starting material and delivers, through a mono-protection strategy, the target compounds in

  一种新的合成方法，用于合成2 - C-甲基-d-赤藓糖醇4-磷酸酯（MEP），它是类异戊二烯的甲羟戊酸非依赖型生物合成途径的关键中间体，及其前体2 - C-甲基-d-赤藓糖醇的氘代类似物描述了乙炔化物。该方法使用2 - C-甲基-d-赤藓糖丙酮化物为起始原料，并通过单保护策略以短方式且高收率递送目标化合物。
• 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。
• Synthesis of 2-<i>C</i>-Methyl-<scp>d</scp>-erythritol 4-Phosphate:  The First Pathway-Specific Intermediate in the Methylerythritol Phosphate Route to Isoprenoids
  作者：Andrew T. Koppisch、Brian S. J. Blagg、C. Dale Poulter

  DOI：10.1021/ol991299x

  日期：2000.1.1

  2-C-Methyl-D-erythritol 4-phosphate (4), formed from 1-deoxy-D-xylulose 5-phosphate (3), is the first pathway-specific intermediate in the methylerythritol phosphate route for the biosynthesis of isoprenoid compounds in bacteria, algae, and plant chloroplasts. In this report, 4 was synthesized from 1,2 propanediol (7) in seven steps with an overall yield of 32% and in an enantiomeric excess of 78%.
• An Efficient Preparation of 2-<i>C</i>-Methyl-<scp>d</scp>-Erythritol 4-Phosphoric Acid and Its Derivatives
  作者：Klaus Kis、Juraithip Wungsintaweekul、Wolfgang Eisenreich、Meinhart H. Zenk、Adelbert Bacher

  DOI：10.1021/jo9905118

  日期：2000.1.1
• Formation of 4-(cytidine 5′-diphospho)-2-C-methyl-d-erythritol from 2-C-methyl-d-erythritol 4-phosphate by 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase, a new enzyme in the nonmevalonate pathway
  作者：Tomohisa Kuzuyama、Motoki Takagi†、Kazuhide Kaneda、Tohru Dairi、Haruo Seto

  DOI：10.1016/s0040-4039(99)02143-7

  日期：2000.1

  2-C-Methyl- D-erythritol-4-phosphate is transformed to 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol in the presence of cytidine 5'-triphosphate by a novel Escherichia coli enzyme, 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, involved in the nonmevalonate pathway. (C) 2000 Elsevier Science Ltd. All rights reserved.