5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[12-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-12-oxododecyl]pentanamide | 1039366-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[12-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-12-oxododecyl]pentanamide
• CAS: 1039366-99-8
• 化学式: C₂₇H₄₄N₄O₆S
• 分子量: 552.736
• InChiKey: FGYILHWEYDHGNQ-QGPPHQKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  175
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1R,5R-1-(12'-azidododecanoyl)-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one 、 (+)生物素-N-琥珀酰亚胺基酯 在 palladium hydroxide - carbon 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 以88%的产率得到5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[12-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-12-oxododecyl]pentanamide
  参考文献：
  名称：

  Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation

  摘要：

  Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell cycle of the human neuroblastoma cell line, SH-SY5Y, at the G1 phase. We have found that epolactaene and its derivatives induce apoptosis in the human leukemia B-cell line, BALL-1. In this study, we prepared fluorescent and biotinylated epolactaene derivatives. We characterized the cellular location and the identification of BALL-1 proteins that reacted with these compounds. The results obtained from the reaction of epolactaene or its derivative with N-acetylcysteine methyl ester indicate that these compounds induce the disulfide formation and the alpha-position of the epoxylactam core is the reactive site. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.029

文献信息

• Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation
  作者：Kouji Kuramochi、Shunsuke Yukizawa、Seiki Ikeda、Takashi Sunoki、Satoshi Arai、Rie Matsui、Akinori Morita、Yoshiyuki Mizushina、Kengo Sakaguchi、Fumio Sugawara、Masahiko Ikekita、Susumu Kobayashi

  DOI：10.1016/j.bmc.2008.03.029

  日期：2008.5

  Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell cycle of the human neuroblastoma cell line, SH-SY5Y, at the G1 phase. We have found that epolactaene and its derivatives induce apoptosis in the human leukemia B-cell line, BALL-1. In this study, we prepared fluorescent and biotinylated epolactaene derivatives. We characterized the cellular location and the identification of BALL-1 proteins that reacted with these compounds. The results obtained from the reaction of epolactaene or its derivative with N-acetylcysteine methyl ester indicate that these compounds induce the disulfide formation and the alpha-position of the epoxylactam core is the reactive site. (c) 2008 Elsevier Ltd. All rights reserved.