5-[2-(8-biotinamido-3,6-dioxaoctyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)benzamido]pentylamine | 328273-45-6

• 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-[2-(8-biotinamido-3,6-dioxaoctyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)benzamido]pentylamine
• CAS: 328273-45-6
• 化学式: C₃₀H₄₄F₃N₇O₆S
• 分子量: 687.784
• InChiKey: CRECWKUIAVIAPB-GVUKDKGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  47.0
• 可旋转键数：
  22.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  177.76
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 5-[2-(8-biotinamido-3,6-dioxaoctyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)benzamido]pentylamine 、 methyl okadaate 在 三乙胺 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 methyl 7-O-[5-[2-(8-biotinamido-3,6-dioxaoctyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)benzamido]pentylcarbamoyl]okadaate
  参考文献：
  名称：

  Development of Biotin–Avidin Technology to Investigate Okadaic Acid-Promoted Cell Signaling Pathway

  摘要：

  Four biotin conjugates of okadaic acid were synthesized for evaluating their interactions with protein phosphatase 2A (PP2A) by surface plasmon resonance (SPR). C7-biotinylated okadaic acid exhibited the strongest binding affinity to the enzyme, while Cl-biotinylated derivative was devoid of affinity. C24- or C27-biotinylated okadaic acid showed moderate affinity to the enzyme. In the wake of this finding, a biotinyl photoaffinity probe was introduced into 7-OH of okadaic acid. Photoaffinity labeling followed by SDS-PAGE analysis indicated that the okadaic acid derivative clearly labeled PP2A. Furthermore, three proteins were also labeled in crude extracts of a marine sponge Halichondria okadai. All these results imply that the C7-biotin conjugate is a versatile reagent for biochemical studies of okadaic acid-binding proteins including PP2A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00752-3
• 作为产物：
  描述：

  Hatanaka reagent 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 生成 5-[2-(8-biotinamido-3,6-dioxaoctyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)benzamido]pentylamine
  参考文献：
  名称：

  Development of Biotin–Avidin Technology to Investigate Okadaic Acid-Promoted Cell Signaling Pathway

  摘要：

  Four biotin conjugates of okadaic acid were synthesized for evaluating their interactions with protein phosphatase 2A (PP2A) by surface plasmon resonance (SPR). C7-biotinylated okadaic acid exhibited the strongest binding affinity to the enzyme, while Cl-biotinylated derivative was devoid of affinity. C24- or C27-biotinylated okadaic acid showed moderate affinity to the enzyme. In the wake of this finding, a biotinyl photoaffinity probe was introduced into 7-OH of okadaic acid. Photoaffinity labeling followed by SDS-PAGE analysis indicated that the okadaic acid derivative clearly labeled PP2A. Furthermore, three proteins were also labeled in crude extracts of a marine sponge Halichondria okadai. All these results imply that the C7-biotin conjugate is a versatile reagent for biochemical studies of okadaic acid-binding proteins including PP2A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00752-3