Ac-Orn(Ac)-Lys(CSNH2)(CSNH2)-Orn(Ac)-NH2 | 1333125-12-4

• 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: Ac-Orn(Ac)-Lys(CSNH2)(CSNH2)-Orn(Ac)-NH2
• 英文别名: (2S)-N-[(2S)-5-acetamido-1-amino-1-oxopentan-2-yl]-6-(carbamothioylamino)-2-[[(2S)-2,5-diacetamidopentanoyl]amino]hexanamide
• CAS: 1333125-12-4
• 化学式: C₂₃H₄₂N₈O₆S
• 分子量: 558.702
• InChiKey: AFEYCURNWWBNQK-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  259
• 氢给体数：
  8
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-acetamidopentanoic acid 在 哌啶 、 Fmoc-Rink resin 、 氨 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N-甲基吗啉 、 甲醇 、 water-d2 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Ac-Orn(Ac)-Lys(CSNH2)(CSNH2)-Orn(Ac)-NH2
  参考文献：
  名称：

  A mechanism-based potent sirtuin inhibitor containing Nε-thiocarbamoyl-lysine (TuAcK)

  摘要：

  In the current study, we have identified N-epsilon-thiocarbamoyl-lysine (TuAcK) as a general sirtuin inhibitory warhead which was shown to be able to confer potent sirtuin inhibition. This inhibition was also shown to be mechanism-based in that the TuAck residue was able to be processed by a sirtuin enzyme with the formation of a stalled S-alkylamidate intermediate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.069

文献信息

• A mechanism-based potent sirtuin inhibitor containing Nε-thiocarbamoyl-lysine (TuAcK)
  作者：Brett M. Hirsch、Yujun Hao、Xiaopeng Li、Chrys Wesdemiotis、Zhenghe Wang、Weiping Zheng

  DOI：10.1016/j.bmcl.2011.06.069

  日期：2011.8

  In the current study, we have identified N-epsilon-thiocarbamoyl-lysine (TuAcK) as a general sirtuin inhibitory warhead which was shown to be able to confer potent sirtuin inhibition. This inhibition was also shown to be mechanism-based in that the TuAck residue was able to be processed by a sirtuin enzyme with the formation of a stalled S-alkylamidate intermediate. (C) 2011 Elsevier Ltd. All rights reserved.