methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-ulosonate | 91294-65-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-ulosonate
• 英文别名: methyl 3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxopropanoate
• CAS: 91294-65-4
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: PJSMAUDVVCCUSG-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-ulosonate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 methyl (methyl 3-deoxy-7-bromo-D-arabino-heptulopyranosid)oate
  参考文献：
  名称：

  Construction of an enzyme-targeted organophosphonate using immobilized enzyme and whole-cell synthesis

  摘要：

  DOI：

  10.1021/ja00285a022
• 作为产物：
  描述：

  2,3-二氟-6-硝基苯胺 在 potassium methanolate 、 magnesium iodide 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-ulosonate
  参考文献：
  名称：

  Synthesis and antibacterial activity of mechanism-based inhibitors of KDO8P synthase and DAH7P synthase

  摘要：

  KDO8PS (3-deOXY-D-manno-2-octulosonate-8-phosphate synthase) and DAH7PS (3-deOXY-D-arabino-2-heptulosonate-7-phosphate synthase) are attractive targets for the development of new anti-infectious agents. Both enzymes appear to proceed via a common mechanism involving the reaction of phosphoenolpyruvate (PEP) with arabinose 5-phosphate or erythrose-4-phosphate, to produce the corresponding ulosonic acids, KDO8P and DAH7P, respectively. The synthesis of new inhibitors closely related to the supposed tetrahedral intermediate substrates for the enzymes is described. The examination of the antibacterial activity of these derivatives is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.019

文献信息

• A straightforward synthesis of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid)
  作者：Ke-Gang Liu、Shou-Gang Hu、Yikang Wu、Zhu-Jun Yao、Yu-Lin Wu

  DOI：10.1039/b205047a

  日期：2002.8.8

  Based on the oxidation of corresponding terminal alkynes to α-keto esters, DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) in its pyranose form and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) in its protected pyranose–furanose mixture form were efficiently synthesized. These terminal alkynes were in turn obtained by C1- or C3-homologation of corresponding protected sugars, respectively. Along with the application of this strategy, the syntheses of two C6-ulosonic acids, 3-deoxy-D-erythro-hex-2-ulosonic acid and 3-deoxy-L-erythro-hex-2-ulosonic acid in their protected pyranose form, were also described.

  基于相应末端炔烃氧化为α-酮酯，成功合成了其吡喃糖形式的DAH（3-脱氧-D-阿拉伯庚-2-尤洛糖酸）和其受保护的吡喃糖-呋喃糖混合形式的DRH（3-脱氧-D-核糖庚-2-尤洛糖酸）。这些末端炔烃则分别通过相应受保护糖的C1或C3同系物化获得。随着这一策略的应用，还描述了两种C6尤洛糖酸的合成，即其受保护的吡喃糖形式的3-脱氧-D-红藓庚-2-尤洛糖酸和3-脱氧-L-红藓庚-2-尤洛糖酸。
• Synthesis and antibacterial activity of mechanism-based inhibitors of KDO8P synthase and DAH7P synthase
  作者：Claude Grison、Sylvain Petek、Chantal Finance、Philippe Coutrot

  DOI：10.1016/j.carres.2004.11.019

  日期：2005.3

  KDO8PS (3-deOXY-D-manno-2-octulosonate-8-phosphate synthase) and DAH7PS (3-deOXY-D-arabino-2-heptulosonate-7-phosphate synthase) are attractive targets for the development of new anti-infectious agents. Both enzymes appear to proceed via a common mechanism involving the reaction of phosphoenolpyruvate (PEP) with arabinose 5-phosphate or erythrose-4-phosphate, to produce the corresponding ulosonic acids, KDO8P and DAH7P, respectively. The synthesis of new inhibitors closely related to the supposed tetrahedral intermediate substrates for the enzymes is described. The examination of the antibacterial activity of these derivatives is reported. (c) 2005 Elsevier Ltd. All rights reserved.
• Construction of an enzyme-targeted organophosphonate using immobilized enzyme and whole-cell synthesis
  作者：L. M. Reimer、D. L. Conley、D. L. Pompliano、J. W. Frost

  DOI：10.1021/ja00285a022

  日期：1986.12