2-(trimethylsilyl)ethyl N6-(2-((2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl)oxy)-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)-L-lysinate | 1233927-55-3

• 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: 2-(trimethylsilyl)ethyl N6-(2-((2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl)oxy)-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)-L-lysinate
• CAS: 1233927-55-3
• 化学式: C₃₁H₅₀F₃N₅O₈Si
• 分子量: 705.847
• InChiKey: KJYXYXUYVCUQKC-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  48.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  172.16
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (+)-7-iso-jasmonoyl-L-isoleucine 、 2-(trimethylsilyl)ethyl N6-(2-((2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl)oxy)-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)-L-lysinate 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以61%的产率得到2-(trimethylsilyl)ethyl N6-(2-((2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl)oxy)-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)-N2-((2-((1R,2S)-3-oxo-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetyl)-L-isoleucyl)-L-lysinate
  参考文献：
  名称：

  Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

  摘要：

  Jasmonates (JAs) are a class of oxylipin compounds that play diverse roles in plant defense and development. The F-box protein coronatine insensitive1 (COI1) plays a crucial role in the JA signaling pathway. To determine whether COI1 binds directly to jasmonates, three biotin-tagged photoaffinity probes for JAs, a jasmonic acid photoaffinity probe (PAJA), a JAIle photoaffinity probe (PAJAIle), and a coronatine photoaffinity probe (PACOR), were designed and synthesized based on analysis of JA structure-activity relationships and molecular modeling of the interaction between COI1 and JAs. Among them, PACOR exhibited the most significant biological activity in inhibiting root growth, promoting accumulation of JA-responsive proteins, and triggering COI1-JAZ1 interaction in Arabidopsis seedlings. PACOR is an effective tool for elucidating the interaction between COI1 and JA. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.059
• 作为产物：
  描述：

  在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80%的产率得到2-(trimethylsilyl)ethyl N6-(2-((2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl)oxy)-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)-L-lysinate
  参考文献：
  名称：

  Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

  摘要：

  Jasmonates (JAs) are a class of oxylipin compounds that play diverse roles in plant defense and development. The F-box protein coronatine insensitive1 (COI1) plays a crucial role in the JA signaling pathway. To determine whether COI1 binds directly to jasmonates, three biotin-tagged photoaffinity probes for JAs, a jasmonic acid photoaffinity probe (PAJA), a JAIle photoaffinity probe (PAJAIle), and a coronatine photoaffinity probe (PACOR), were designed and synthesized based on analysis of JA structure-activity relationships and molecular modeling of the interaction between COI1 and JAs. Among them, PACOR exhibited the most significant biological activity in inhibiting root growth, promoting accumulation of JA-responsive proteins, and triggering COI1-JAZ1 interaction in Arabidopsis seedlings. PACOR is an effective tool for elucidating the interaction between COI1 and JA. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.059