(S)-2-Amino-N-{2-[2-((S)-2-amino-3-methyl-butyrylamino)-ethyldisulfanyl]-ethyl}-3-methyl-butyramide | 390424-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Amino-N-{2-[2-((S)-2-amino-3-methyl-butyrylamino)-ethyldisulfanyl]-ethyl}-3-methyl-butyramide
• CAS: 390424-56-3
• 化学式: C₁₄H₃₀N₄O₂S₂
• 分子量: 350.55
• InChiKey: QCWNIQWXORILSF-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  110.24
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  BOC-甘氨酸 、 (S)-2-Amino-N-{2-[2-((S)-2-amino-3-methyl-butyrylamino)-ethyldisulfanyl]-ethyl}-3-methyl-butyramide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.33h， 以60%的产率得到{[(S)-1-(2-{2-[(S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-ethyldisulfanyl}-ethylcarbamoyl)-2-methyl-propylcarbamoyl]-methyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  伪β桶的发现：通过二茂铁环肽的平铺合成和形成。

  摘要：

  DOI：

  10.1002/anie.200502788
• 作为产物：
  描述：

  [Boc-Val-CSA]2 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-2-Amino-N-{2-[2-((S)-2-amino-3-methyl-butyrylamino)-ethyldisulfanyl]-ethyl}-3-methyl-butyramide
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3