dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate | 90357-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate
• 英文别名: dibenzyl [(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] phosphate
• CAS: 90357-98-5
• 化学式: C₄₈H₄₉O₉P
• 分子量: 800.885
• InChiKey: XWMQVWWDTJCKIV-ZEWOKLPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 在 氨 、 sodium 作用下， 生成 mannose-1-phosphate
  参考文献：
  名称：

  Pallanca, Jane E.; Turner, Nicolas J., Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3017 - 3022

  摘要：

  DOI：
• 作为产物：
  描述：

  焦磷酸四苄酯 、 2,3,4,6-tetra-O-benzyl-D-mannopyranose 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙基苯 为溶剂， 反应 3.0h， 以95%的产率得到dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate
  参考文献：
  名称：

  The cofactor Mg2+—a key switch for effective continuous enzymatic production of GDP-mannose using recombinant GDP-mannose pyrophosphorylase

  摘要：

  The aim of the presented work is the chemoenzymatic synthesis of GDP-mannose (GDP-Man). Mannose-l-phosphate (Man-l-P) is synthesised by a very convenient chemical method and is activated with GTP and recombinant GDP-mannose pyrophosphorylase (GDP-Man PP) to give GDP-Man, The productivity of the process is improved using reaction engineering techniques. Detailed kinetic studies, modelling of the reaction and simulations of different reaction systems revealed that besides a strong product inhibition the cofactor Mg2+ is a key switch for effective enzymatic synthesis. Using a two-stage cascade of enzyme membrane reactors, GDP-Man could be produced continuously with a space-time yield of 28 g L-1 d(-1) and an enzyme consumption of 0.9 U g(-1), which means a six-fold improvement related to batch synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10095-7

文献信息

• Chemical Synthesis of <scp>d</scp>-<i>glycero</i>-<scp>d</scp>-<i>manno</i>-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation
  作者：Shinsuke Inuki、Toshihiko Aiba、Shota Kawakami、Taishin Akiyama、Jun-ichiro Inoue、Yukari Fujimoto

  DOI：10.1021/acs.orglett.7b01158

  日期：2017.6.16

  and glycolipids. HBP β-anomer was recently reported to be a pathogen-associated molecular pattern (PAMP) that regulates TIFA-dependent immunity. Herein, we report the chemical synthesis of HBP α- and β-anomers, which highlights a C-7 carbon homologation via the Corey–Chaykovsky reaction, and the introduction of a phosphate group at the anomeric position using the Mitsunobu reaction. Furthermore, NF-κB

  d -甘油基- d -甘露-Heptose 1,7-二磷酸（HBP）是庚糖残基的前体在革兰氏阴性细菌膜表面糖蛋白和糖脂中。最近报道，HBPβ-异头物是一种病原体相关分子模式（PAMP），可调节TIFA依赖性免疫。在这里，我们报道了HBPα-和β-端基异构体的化学合成，该反应突出了通过Corey-Chaykovsky反应的C-7碳同系物，以及使用Mitsunobu反应在端基异构体位置引入了磷酸基团。此外，NF-κB报告基因检测表明，HBPβ-异头物激活了NF-κB信号传导途径。
• Hung, Shang-Cheng; Wong, Chi-Huey, Angewandte Chemie, 1996, vol. 108, # 22, p. 2829 - 2832
  作者：Hung, Shang-Cheng、Wong, Chi-Huey

  DOI：——

  日期：——
• Schmidt, Richard R.; Stumpp, Michael, Liebigs Annalen der Chemie, 1984, # 4, p. 680 - 691
  作者：Schmidt, Richard R.、Stumpp, Michael

  DOI：——

  日期：——
• Pallanca, Jane E.; Turner, Nicolas J., Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3017 - 3022
  作者：Pallanca, Jane E.、Turner, Nicolas J.

  DOI：——

  日期：——
• The cofactor Mg2+—a key switch for effective continuous enzymatic production of GDP-mannose using recombinant GDP-mannose pyrophosphorylase
  作者：Sven Fey、Lothar Elling、Udo Kragl

  DOI：10.1016/s0008-6215(97)10095-7

  日期：1997.12

  The aim of the presented work is the chemoenzymatic synthesis of GDP-mannose (GDP-Man). Mannose-l-phosphate (Man-l-P) is synthesised by a very convenient chemical method and is activated with GTP and recombinant GDP-mannose pyrophosphorylase (GDP-Man PP) to give GDP-Man, The productivity of the process is improved using reaction engineering techniques. Detailed kinetic studies, modelling of the reaction and simulations of different reaction systems revealed that besides a strong product inhibition the cofactor Mg2+ is a key switch for effective enzymatic synthesis. Using a two-stage cascade of enzyme membrane reactors, GDP-Man could be produced continuously with a space-time yield of 28 g L-1 d(-1) and an enzyme consumption of 0.9 U g(-1), which means a six-fold improvement related to batch synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.