D-Glycero-D-manno-Heptose 7-phosphate

• 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: D-Glycero-D-manno-Heptose 7-phosphate
• 英文别名: 7-phosphate-D-glycero-β-D-mannoheptose；D-glycero-D-manno-heptopyranose-7-phosphate；7-O-phosphono-D-glycero-beta-D-manno-heptopyranose；[(2R)-2-hydroxy-2-[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]ethyl] dihydrogen phosphate
• 化学式: C₇H₁₅O₁₀P
• 分子量: 290.164
• InChiKey: SDADNVAZGVDAIM-ZUHYCWGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  D-Glycero-D-manno-Heptose 7-phosphate 、 5’-三磷酸腺苷 在 无机焦磷酸酶 、 HIdE 、 phosphatase GmhB 、 sodium hydroxide 、 magnesium chloride 、 alkaline phosphatase 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 以42%的产率得到adenosine 5′-diphosphate-d-glycero-β-d-manno-heptopyranose
  参考文献：
  名称：

  Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

  摘要：

  An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-beta-D-mannoheptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.12.019
• 作为产物：
  描述：

  benzyl 7-O-dibenzyl-phosphono-2,3,4,6-O-tetra-benzyl-D-glycero-α-D-manno-heptopyranoside 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以92%的产率得到D-Glycero-D-manno-Heptose 7-phosphate
  参考文献：
  名称：

  Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

  摘要：

  An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-beta-D-mannoheptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.12.019

文献信息

• Systematic Synthesis of Inhibitors of the Two First Enzymes of the Bacterial Heptose Biosynthetic Pathway: Towards Antivirulence Molecules Targeting Lipopolysaccharide Biosynthesis
  作者：Maxime Durka、Abdellatif Tikad、Régis Périon、Michael Bosco、Mounir Andaloussi、Stéphanie Floquet、Elodie Malacain、François Moreau、Mayalen Oxoby、Vincent Gerusz、Stéphane P. Vincent

  DOI：10.1002/chem.201100396

  日期：2011.9.26

  for the development of antivirulence drugs. We report the synthesis of a series of D‐glycero‐D‐manno‐heptopyranose 7‐phosphate (H7P) analogues and their inhibition properties against the isomerase GmhA and the the kinase HldE, the two first enzymes of the bacterial heptose biosynthetic pathway. The heptose structures have been modified at the 1‐, 2‐, 6‐ and 7‐positions to probe the importance of the

  大号-Heptoses（大号-甘油基- d -甘露-heptopyranoses）的脂多糖（LPS）的内芯的成分，在许多传染性疾病，以及在许多人类病原体毒力的死亡率分子发挥关键作用。迄今为止，抑制细菌庚糖生物合成途径的第一种酶的方法几乎是一个尚未开发的领域，尽管它似乎是开发抗毒药物的一种非常新颖的方法。我们报告了一系列的合成d -甘油- d -甘露七磷酸吡喃葡萄糖（H7P）类似物及其对异构酶GmhA和激酶HldE的抑制特性，所述细菌是细菌庚糖生物合成途径的两个首个酶。庚糖的结构已在1、2、6和7位进行了修饰，以探究H7P关键结构特征的重要性，这些特征允许与目标酶紧密结合。H7P是GmhA和HldE底物的产物，第二个目标是寻找可以同时抑制两种酶的结构。我们发现GmhA和HldE对庚糖支架6位和7位的结构修饰极为敏感。令我们惊讶的是，H7P的差向异构体显示D-glucopyranose配置被认
• Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE
  作者：Tiehai Li、Liuqing Wen、Adriel Williams、Baolin Wu、Lei Li、Jingyao Qu、Jeffrey Meisner、Zhongying Xiao、Junqiang Fang、Peng George Wang

  DOI：10.1016/j.bmc.2013.12.019

  日期：2014.2

  An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-beta-D-mannoheptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.