methyl 6,7-dideoxy-7-diethoxyphosphoryl-α-D-glucoheptopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6,7-dideoxy-7-diethoxyphosphoryl-α-D-glucoheptopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(2-diethoxyphosphorylethyl)-6-methoxyoxane-3,4,5-triol
• 化学式: C₁₂H₂₅O₈P
• 分子量: 328.299
• InChiKey: VHFMHKTZQPBBHX-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6,7-dideoxy-7-diethoxyphosphoryl-α-D-glucoheptopyranoside 在 甲醇 、 水 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 23.0h， 生成 methyl 6,7-dideoxy-7-phosphoryl-α-D-glucoheptopyranoside bis lithium salt
  参考文献：
  名称：

  α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase

  摘要：

  Glucose-6-phosphatase (G6Pase) is an essential metabolic enzyme that has upregulated activity in Type II diabetes. Synthetic analogs of the G6Pase substrate, glucose-6-phosphate (G6P), may provide new tools to probe enzyme activity, or lead to specific inhibitors of glycosylphosphatase enzymes. Here we have developed synthetic routes to a panel of non-hydrolyzable G6P analogs containing alpha-bromo,alpha,alpha-dibromo, and alpha-bromo-alpha, beta-unsaturated phosphonates compatible with a carbohydrate nucleus. We confirm that these functionalities have potency as inhibitors of G6Pase in vitro, providing a series of new phosphate isosteres that can be exploited for inhibitor design. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.003
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-glucuronic acid 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 1.17h， 生成 methyl 6,7-dideoxy-7-diethoxyphosphoryl-α-D-glucoheptopyranoside
  参考文献：
  名称：

  α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase

  摘要：

  Glucose-6-phosphatase (G6Pase) is an essential metabolic enzyme that has upregulated activity in Type II diabetes. Synthetic analogs of the G6Pase substrate, glucose-6-phosphate (G6P), may provide new tools to probe enzyme activity, or lead to specific inhibitors of glycosylphosphatase enzymes. Here we have developed synthetic routes to a panel of non-hydrolyzable G6P analogs containing alpha-bromo,alpha,alpha-dibromo, and alpha-bromo-alpha, beta-unsaturated phosphonates compatible with a carbohydrate nucleus. We confirm that these functionalities have potency as inhibitors of G6Pase in vitro, providing a series of new phosphate isosteres that can be exploited for inhibitor design. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.003

文献信息

• α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase
  作者：A. Michael Downey、Christopher W. Cairo

  DOI：10.1016/j.carres.2013.08.003

  日期：2013.11

  Glucose-6-phosphatase (G6Pase) is an essential metabolic enzyme that has upregulated activity in Type II diabetes. Synthetic analogs of the G6Pase substrate, glucose-6-phosphate (G6P), may provide new tools to probe enzyme activity, or lead to specific inhibitors of glycosylphosphatase enzymes. Here we have developed synthetic routes to a panel of non-hydrolyzable G6P analogs containing alpha-bromo,alpha,alpha-dibromo, and alpha-bromo-alpha, beta-unsaturated phosphonates compatible with a carbohydrate nucleus. We confirm that these functionalities have potency as inhibitors of G6Pase in vitro, providing a series of new phosphate isosteres that can be exploited for inhibitor design. (C) 2013 Elsevier Ltd. All rights reserved.