(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hexadecyloxy-propan-1-ol | 119907-63-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hexadecyloxy-propan-1-ol
• 英文别名: (S)-3-(tert-butyldiphenylsilyloxy)-2-(hexadecyloxy)propan-1-ol
• CAS: 119907-63-0；119879-79-7
• 化学式: C₃₅H₅₈O₃Si
• 分子量: 554.929
• InChiKey: LVQSXYKNOGKTFO-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  39.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hexadecyloxy-propan-1-ol 在 四氮唑 、 重铬酸吡啶 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 双氧水 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 58.83h， 生成
  参考文献：
  名称：

  Synthesis of Modified Peptidoglycan Precursor Analogues for the Inhibition of Glycosyltransferase

  摘要：

  The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of On OH glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(L-Alao-D-Glu)-GIcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.

  DOI：

  10.1021/ja302099u
• 作为产物：
  描述：

  (S)-1-(tert-butyldiphenylsilyloxy)-3-(4'-methoxybenzyloxy)propan-2-ol 在 四丁基碘化铵 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hexadecyloxy-propan-1-ol
  参考文献：
  名称：

  Synthesis of Modified Peptidoglycan Precursor Analogues for the Inhibition of Glycosyltransferase

  摘要：

  The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of On OH glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(L-Alao-D-Glu)-GIcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.

  DOI：

  10.1021/ja302099u

文献信息

• Glycidyl derivatives as chiral C3 synthons. Ring opening catalyzed by boron trifluoride etherate
  作者：Pedro N. Guivisdalsky、Robert Bittman

  DOI：10.1021/ja00190a059

  日期：1989.4