biotin-Ser-Gln-Asn-Tyr-Pro-Ile-Val-Phe-OH | 1262241-22-4

• 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: biotin-Ser-Gln-Asn-Tyr-Pro-Ile-Val-Phe-OH
• CAS: 1262241-22-4
• 化学式: C₅₆H₈₀N₁₂O₁₅S
• 分子量: 1193.39
• InChiKey: UQTKYGFJEUCPSV-PJVPECLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.79
• 重原子数：
  84.0
• 可旋转键数：
  33.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  429.08
• 氢给体数：
  14.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  biotin-Ser-Gln-Asn-Tyr-Pro-Ile-Val-Phe-OH 、 (S)-2-amino-4-methyl-N-(4-methyl-2-oxo-2H-chromen-7-yl)pentanamide 2,2,2-trifluoroacetate 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以73%的产率得到
  参考文献：
  名称：

  HIV Protease-Mediated Activation of Sterically Capped Proteasome Inhibitors and Substrates

  摘要：

  Strategies for selectively killing HIV-infected cells present an appealing alternative to traditional antiretroviral drugs. We show here the first example of an inactive "Trojan horse" molecule that releases a cytotoxic, small-molecule proteasome inhibitor upon cleavage by HIV-1 protease. As a proof-of-concept strategy, the protein avidin was used to block entry of the compound into the proteasome in the absence of HIV-1 protease. We demonstrate that this strategy is also feasible without requiring an exogenous protein; a polylysine dendrimer-containing molecule is unable to enter the proteasome until cleaved by HIV-1 protease. These results demonstrate that conditional proteasome inhibitors could prove useful in the development of new tools for chemical biology and future therapeutics.

  DOI：

  10.1021/ja109377p