[(3R,4S,5R,8S,9S,12R)-5,9-dihydroxy-4-methoxy-12-[(2S,3S,6R,8S,9R)-8-[(3S,4Z)-4-[2-[2-[[2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]ethylamino]-2-oxoethoxy]imino-3-methylpentyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,8-dimethyl-7-oxotridecan-3-yl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate | 679406-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3R,4S,5R,8S,9S,12R)-5,9-dihydroxy-4-methoxy-12-[(2S,3S,6R,8S,9R)-8-[(3S,4Z)-4-[2-[2-[[2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]ethylamino]-2-oxoethoxy]imino-3-methylpentyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,8-dimethyl-7-oxotridecan-3-yl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
• CAS: 679406-23-6
• 化学式: C₅₅H₈₀F₃N₅O₁₆
• 分子量: 1124.26
• InChiKey: VWGUBEOEXBIQIJ-BNKTXJBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  79
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  289
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  [(3R,4S,5R,8S,9S,12R)-5,9-dihydroxy-4-methoxy-12-[(2S,3S,6R,8S,9R)-8-[(3S,4Z)-4-[2-[2-[[2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]ethylamino]-2-oxoethoxy]imino-3-methylpentyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,8-dimethyl-7-oxotridecan-3-yl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 生成 (Z)-2-[(1R)-3-[(3R,4S,5R,8S,9S,12R)-5,9-dihydroxy-4-methoxy-12-[(2S,3S,6R,8S,9R)-8-[(3S,4Z)-4-[2-[2-[[2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]ethylamino]-2-oxoethoxy]imino-3-methylpentyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,8-dimethyl-7-oxotridecan-3-yl]oxy-1-hydroxy-3-oxopropyl]-3-methylbut-2-enedioic acid
  参考文献：
  名称：

  Protein phosphatase inhibitory activity of tautomycin photoaffinity probes evaluated at femto-molar level

  摘要：

  Herein we describe the further improvement of our in-house developed firefly bioluminescence assay system for the determination of inhibition of protein phosphatase (PP). The advantage with the new system is higher sensitivity as well as being time and sample efficient. The inhibition activity of tautomycin with PP1 gamma was determined using the upgraded test system and K-i was found to be 4.5 nM, which compare favorably with the activity reported previously by others using different methods. The test system was then used in order to determine the activity of nine tautomycin (TTM) photoaffinity probes. One of the TTM photoaffinity probes (anti-10) was found to possess higher activity than the natural product itself with a K-i of 3.4 nM, while the remaining photoaffinity probes were found to possess K-i in the range of 8.0-213 nM. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.034
• 作为产物：
  描述：

  N-(2-amino-ethyl)-2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzamide 在 sodium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 [(3R,4S,5R,8S,9S,12R)-5,9-dihydroxy-4-methoxy-12-[(2S,3S,6R,8S,9R)-8-[(3S,4Z)-4-[2-[2-[[2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]ethylamino]-2-oxoethoxy]imino-3-methylpentyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,8-dimethyl-7-oxotridecan-3-yl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
  参考文献：
  名称：

  Synthesis of photoaffinity probes of tautomycin

  摘要：

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.053

文献信息

• Synthesis of photoaffinity probes of tautomycin
  作者：Masakuni Kurono、Aya Shimomura、Minoru Isobe

  DOI：10.1016/j.tet.2003.12.053

  日期：2004.2

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.
• Protein phosphatase inhibitory activity of tautomycin photoaffinity probes evaluated at femto-molar level
  作者：Magne O. Sydnes、Masaki Kuse、Masakuni Kurono、Aya Shimomura、Hiroshi Ohinata、Akira Takai、Minoru Isobe

  DOI：10.1016/j.bmc.2007.11.034

  日期：2008.2

  Herein we describe the further improvement of our in-house developed firefly bioluminescence assay system for the determination of inhibition of protein phosphatase (PP). The advantage with the new system is higher sensitivity as well as being time and sample efficient. The inhibition activity of tautomycin with PP1 gamma was determined using the upgraded test system and K-i was found to be 4.5 nM, which compare favorably with the activity reported previously by others using different methods. The test system was then used in order to determine the activity of nine tautomycin (TTM) photoaffinity probes. One of the TTM photoaffinity probes (anti-10) was found to possess higher activity than the natural product itself with a K-i of 3.4 nM, while the remaining photoaffinity probes were found to possess K-i in the range of 8.0-213 nM. (C) 2007 Elsevier Ltd. All rights reserved.