(3S)-Boc-L-valine-(4S)-methyl-N-O-benzylsuccinimide | 182007-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-Boc-L-valine-(4S)-methyl-N-O-benzylsuccinimide
• 英文别名: tert-butyl N-[(2S)-3-methyl-1-[(3R,4S)-4-methyl-2,5-dioxo-1-phenylmethoxypyrrolidin-3-yl]-1-oxobutan-2-yl]carbamate
• CAS: 182007-77-8
• 化学式: C₂₂H₃₀N₂O₆
• 分子量: 418.49
• InChiKey: LGGIGDFBALMDRT-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-Boc-L-valine-(4S)-methyl-N-O-benzylsuccinimide 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 2-溴苯乙酮 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 tert-butyl ((S)-3-methyl-1-((3R,4S)-4-methyl-2,5-dioxopyrrolidin-3-yl)-1-oxobutan-2-yl)carbamate
  参考文献：
  名称：

  山梨酸尾部对 Moiramide B 抗菌和抗结核特性作用的再研究

  摘要：

  新子口袋：在这项研究中，我们证明了假肽 moiramide B 的山梨酸尾部对于乙酰辅酶 A 羧化酶结合是必不可少的。基于结构-活性和分子建模数据，为 N-末端修饰的莫拉酰胺衍生物开发了结合模型。

  DOI：

  10.1002/cmdc.202200631
• 作为产物：
  描述：

  (S)-4-(叔丁氧基)-2-甲基-4-氧代丁酸 在 乙酰氯 、 N,N'-羰基二咪唑 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (3S)-Boc-L-valine-(4S)-methyl-N-O-benzylsuccinimide
  参考文献：
  名称：

  Asymmetric synthesis of moiramide B

  摘要：

  使用锂酰胺 4 和吡咯烷酮助剂 5 首次不对称合成了 Moiramide B 1；利用吡咯烷酮助剂 5 生成新型 (S)-2-甲基-N-苄氧基琥珀酰亚胺 15，随后在强碱性条件下与高活性叔丁氧羰基保护的 L-缬氨酸 N-甲酸酐（Boc-Val-NCA）酰化，而不会发生外消旋化，同时利用锂酰胺 4 合成同手性 D-β-苯丙氨酸叔丁酯 8。

  DOI：

  10.1039/cc9960001797

文献信息

• Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase
  作者：Molly A. Silvers、Gregory T. Robertson、Carol M. Taylor、Grover L. Waldrop

  DOI：10.1021/jm501082n

  日期：2014.11.13

  There is an urgent demand for the development of new antibiotics due to the increase in drug-resistant pathogenic bacteria. A novel target is the multifunctional enzyme acetyl-CoA carboxylase (ACC), which catalyzes the first committed step in fatty acid synthesis and consists of two enzymes: biotin carboxylase and carboxyltransferase. Covalently attaching known inhibitors against these enzymes with saturated hydrocarbon linkers of different lengths generated dual-ligand inhibitors. Kinetic results revealed that the dual-ligands inhibited the ACC complex in the nanomolar range. Microbiology assays showed that the dual-ligand with a 15-carbon linker did not exhibit any antibacterial activity, while the dual-ligand with a 7-carbon linker displayed broad-spectrum antibacterial activity as well as a decreased susceptibility in the development of bacterial resistance. These results suggest that the properties of the linker are vital for antibacterial activity and show how inhibiting two different enzymes with the same compound increases the overall potency while also impeding the development of resistance.
• Pyrrolidinedione derivatives as antibacterial agents with a novel mode of action
  作者：Jens Pohlmann、Thomas Lampe、Mitsuyuki Shimada、Peter G. Nell、Josef Pernerstorfer、Niels Svenstrup、Nina A. Brunner、Guido Schiffer、Christoph Freiberg

  DOI：10.1016/j.bmcl.2004.12.002

  日期：2005.2

  The pseudopeptide pyrrolidinedione natural products moiramide B and andrimid represent a new class of antibiotics that target bacterial fatty acid biosynthesis. Structure activity relationship (SAR) studies revealed a high degree of variability for the fatty acid side chain, allowing optimization of physicochemical parameters, and a restricted SAR for the pyrrolidinedione group, indicating major relevance of this subunit for efficient target binding. (C) 2004 Elsevier Ltd. All rights reserved.
• Davies, Stephen G.; Dixon, Darren J., Journal of the Chemical Society. Perkin transactions I, 1998, # 17, p. 2635 - 2643
  作者：Davies, Stephen G.、Dixon, Darren J.

  DOI：——

  日期：——