[Boc-Val-CSA]2 | 728915-71-7

• 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: [Boc-Val-CSA]2
• 英文别名: [Boc-Val-cysteamine]2
• CAS: 728915-71-7
• 化学式: C₂₄H₄₆N₄O₆S₂
• 分子量: 550.784
• InChiKey: FNMSBJZBYDUGLF-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  134.86
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [Boc-Val-CSA]2 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 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.83h， 生成 {[(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-L-缬氨酸羟基琥珀酰亚胺酯 、 cystamine dihydrochioride 在 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.0h， 生成 [Boc-Val-CSA]2
  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

文献信息

• Synthesis, structure and electrochemistry of ferrocene–peptide macrocycles
  作者：Somenath Chowdhury、Gabriele Schatte、Heinz-Bernhard Kraatz

  DOI：10.1039/b401039f

  日期：——

  Redox active cyclopeptides Fc[CSA]2 (5), Fc[Gly–CSA]2 (6), Fc[Ala–CSA]2 (7), Fc[Val–CSA]2 (8) and Fc[Leu–CSA]2 (9) (CSA = cysteamine) which are formed by the reaction of ferrocenedicarboxylic acid with peptide cystamines at high dilutions. These systems exhibit H-bonding involving the amide NH in solution as shown by their temperature dependent NMR spectra. With the exception of 5, the ferrocene macrocycles display intramolecular N⋯O cross-ring H-bonding in the solid state involving the amino acids proximal to the ferrocene.

  氧化还原活性环肽 Fc[CSA]2 (5)、Fc[GlyâCSA]2 (6)、Fc[AlaâCSA]2 (7)、Fc[ValâCSA]2 (8) 和 Fc[LeuâCSA]2 (9)（CSA = 半胱胺）是二茂铁二羧酸与肽胱胺在高稀释度下反应生成的。这些体系在溶液中表现出涉及酰胺 NH 的 H 键，这一点可以从它们与温度相关的 NMR 光谱中看出。除 5 外，二茂铁大环在固态下显示出分子内 Nâ¯O 跨环 H 键，涉及二茂铁附近的氨基酸。