9-fluorenylmethoxycarbonyl-4-amino-1-oxyl-2,2,6,6,-tetramethylpiperidine-4-carboxylic acid | 1423037-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-fluorenylmethoxycarbonyl-4-amino-1-oxyl-2,2,6,6,-tetramethylpiperidine-4-carboxylic acid
• 英文别名: Fmoc-TOAC；Fmoc-2,2,6,6-tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic Acid；4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-hydroxy-2,2,6,6-tetramethylpiperidine-4-carboxylic acid
• CAS: 1423037-36-8
• 化学式: C₂₅H₃₀N₂O₅
• 分子量: 438.524
• InChiKey: FDFQTZLNQLBAIC-UHFFFAOYSA-N

物化性质

• 沸点：
  639.1±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chlorotrityl-Ala-H polystyrene resin 、 Fmoc-L-丙氨酸 、 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin 、 9-fluorenylmethoxycarbonyl-4-amino-1-oxyl-2,2,6,6,-tetramethylpiperidine-4-carboxylic acid 、 Fmoc-2-氨基异丁酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以49%的产率得到TPP-(Ala-Aib)₄-Ala-TOAC-Ala-(Aib-Ala)₂-OH
  参考文献：
  名称：

  Porphyrin Triplet State as a Potential Spin Label for Nanometer Distance Measurements by PELDOR Spectroscopy

  摘要：

  This work demonstrates, for the first time, the feasibility of applying pulsed electron-electron double resonance (PELDOR/DEER) to determine the interspin distance between a photoexcited porphyrin triplet state (S = 1) and a nitroxide spin label chemically incorporated into a small helical peptide. The PELDOR trace shows deep envelope modulation induced by electron electron dipole interaction between the partners in the pair, providing an accurate distance measurement. This new labeling approach has a high potential for measuring nanometer distances in more complex biological systems due to the sensitivity acquired from the spin polarization of the photoexcited triplet state spectrum.

  DOI：

  10.1021/ja502615n

文献信息

• Porphyrin Triplet State as a Potential Spin Label for Nanometer Distance Measurements by PELDOR Spectroscopy
  作者：Marilena Di Valentin、Marco Albertini、Enrico Zurlo、Marina Gobbo、Donatella Carbonera

  DOI：10.1021/ja502615n

  日期：2014.5.7

  This work demonstrates, for the first time, the feasibility of applying pulsed electron-electron double resonance (PELDOR/DEER) to determine the interspin distance between a photoexcited porphyrin triplet state (S = 1) and a nitroxide spin label chemically incorporated into a small helical peptide. The PELDOR trace shows deep envelope modulation induced by electron electron dipole interaction between the partners in the pair, providing an accurate distance measurement. This new labeling approach has a high potential for measuring nanometer distances in more complex biological systems due to the sensitivity acquired from the spin polarization of the photoexcited triplet state spectrum.