| 247068-77-5

• 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
• CAS: 247068-77-5
• 化学式: C₅₅H₆₇N₃O₇Si
• 分子量: 910.238
• InChiKey: ZBYGHWXPKBTNRA-OYIIPAFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.01
• 重原子数：
  66.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以98%的产率得到(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-((2S,3S)-2-{(2S,3S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-methyl-pentanoylamino}-3-methyl-pentanoylamino)-butyric acid
  参考文献：
  名称：

  Total synthesis of the-potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology

  摘要：

  Epoxomicin (1), a peptide alpha',beta'-epoxyketone isolated from the actinomycete strain No.Q996-17, possesses potent in vivo anti-tumor and anti-inflammatory activities. In this paper, we report the first syntheses of epoxomicin, [H-3]-epoxomicin, and a biotinylated epoxomicin analog as well as the absolute configuration of the epoxide stereocenter. The natural product and derivatives have permitted the first identification of the proteasome as the specific cellular target of epoxomicin. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00376-5
• 作为产物：
  描述：

  L-苏氨酸苯甲酯 在 哌啶 、 咪唑 、 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 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.33h， 生成
  参考文献：
  名称：

  Total synthesis of the-potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology

  摘要：

  Epoxomicin (1), a peptide alpha',beta'-epoxyketone isolated from the actinomycete strain No.Q996-17, possesses potent in vivo anti-tumor and anti-inflammatory activities. In this paper, we report the first syntheses of epoxomicin, [H-3]-epoxomicin, and a biotinylated epoxomicin analog as well as the absolute configuration of the epoxide stereocenter. The natural product and derivatives have permitted the first identification of the proteasome as the specific cellular target of epoxomicin. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00376-5

文献信息

• Enzyme inhibition
  申请人：Yale University

  公开号：US06831099B1

  公开（公告）日：2004-12-14

  Peptide-based compounds including heteroatom-containing, three-membered rings efficiently and selectively inhibit specific activities of N-terminal nucleophile (Ntn) hydrolases. The activities of those Ntn having multiple activities can be differentially inhibited by the compounds described. For example, the chymotrypsin-like and PGPH activities of the 20S proteasome can be selectively inhibited with the inventive compounds. The peptide-based compounds include an electron withdrawing group adjacent to the ring functionality, and the peptide include at least three peptide units. Among other therapeutic utilities, the peptide-based compounds exhibit anti-inflammatory and inhibition of cell proliferation, involving therapeutic applications for these compounds.

  肽基化合物，包括含杂原子的三元环，能高效且特异性地抑制N端核苷酸（Ntn）水解酶的特定活性。这些具有多种活性的Ntn水解酶的活性可以通过所描述的化合物得到差异性抑制。例如，20S蛋白酶体的糜蛋白酶样和PGPH活性可以通过这些创新化合物被选择性抑制。这些肽基化合物包含一个与环功能性相邻的吸电子基团，并且肽链至少包含三个肽单元。在其他治疗用途之外，这些肽基化合物表现出抗炎和抑制细胞增殖的作用，涉及这些化合物的治疗应用。