allyl N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionate | 845255-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionate
• 英文别名: prop-2-enyl (2S)-3-[6-(dimethylamino)-1,3-dioxobenzo[f]isoindol-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 845255-78-9
• 化学式: C₃₅H₃₁N₃O₆
• 分子量: 589.648
• InChiKey: RMAQZEUIYJCCFA-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionate 在 四(三苯基膦)钯 、 苯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以210 mg的产率得到N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionic acid
  参考文献：
  名称：

  Photophysics and Biological Applications of the Environment-Sensitive Fluorophore 6-N,N-Dimethylamino-2,3-naphthalimide

  摘要：

  We have synthesized a new environment-sensitive fluorophore, 6-N,N-dimethylamino-2,3-naphthalimide (6DMN). This chromophore exhibits valuable fluorescent properties as a biological probe with emission in the 500-600 nm range and a marked response to changes in the environment polarity. The 6DMN fluorescence is red-shifted in polar protic environments, with the maximum emission intensity shifting more than 100 nm from 491 nm in toluene to 592 nm in water. Additionally, the fluorescence quantum yield decreases more than 100-fold from chloroform (Phi = 0.225) to water (Phi = 0.002). The scope and applications of the 6DMN probe are expanded with the synthesis of an Fmoc-protected amino acid derivative (5), which contains the fluorophore. This unnatural amino acid has been introduced into several peptides, demonstrating that it can be manipulated under standard solid-phase peptide synthesis conditions. Peptides incorporating the new residue can be implemented for monitoring protein-protein interactions as exemplified in studies with Sire homology 2 (SH2) phosphotyrosine binding domains. The designed peptides exhibit a significant increase in the quantum yield of the long wavelength fluorescence emission band (596 nm) upon binding to selected SH2 domains (e.g., Crk SH2, Abl SH2, and PI3K SH2). The peptides can be used as ratiometric sensors, since the short wavelength band (460 nm) was found almost invariable throughout the titrations.

  DOI：

  10.1021/ja0449168
• 作为产物：
  描述：

  6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 allyl N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionate
  参考文献：
  名称：

  Photophysics and Biological Applications of the Environment-Sensitive Fluorophore 6-N,N-Dimethylamino-2,3-naphthalimide

  摘要：

  We have synthesized a new environment-sensitive fluorophore, 6-N,N-dimethylamino-2,3-naphthalimide (6DMN). This chromophore exhibits valuable fluorescent properties as a biological probe with emission in the 500-600 nm range and a marked response to changes in the environment polarity. The 6DMN fluorescence is red-shifted in polar protic environments, with the maximum emission intensity shifting more than 100 nm from 491 nm in toluene to 592 nm in water. Additionally, the fluorescence quantum yield decreases more than 100-fold from chloroform (Phi = 0.225) to water (Phi = 0.002). The scope and applications of the 6DMN probe are expanded with the synthesis of an Fmoc-protected amino acid derivative (5), which contains the fluorophore. This unnatural amino acid has been introduced into several peptides, demonstrating that it can be manipulated under standard solid-phase peptide synthesis conditions. Peptides incorporating the new residue can be implemented for monitoring protein-protein interactions as exemplified in studies with Sire homology 2 (SH2) phosphotyrosine binding domains. The designed peptides exhibit a significant increase in the quantum yield of the long wavelength fluorescence emission band (596 nm) upon binding to selected SH2 domains (e.g., Crk SH2, Abl SH2, and PI3K SH2). The peptides can be used as ratiometric sensors, since the short wavelength band (460 nm) was found almost invariable throughout the titrations.

  DOI：

  10.1021/ja0449168

文献信息

• FLUORESCENT PROBES FOR BIOLOGICAL STUDIES
  申请人：Imperiali Barbara

  公开号：US20090082577A1

  公开（公告）日：2009-03-26

  The present invention provides fluorescent compounds of formula (I) and methods monitoring protein-protein interactions.

  本发明提供了式(I)的荧光化合物和监测蛋白质相互作用的方法。
• US7442529B2
  申请人：——

  公开号：US7442529B2

  公开（公告）日：2008-10-28
• Photophysics and Biological Applications of the Environment-Sensitive Fluorophore 6-<i>N</i>,<i>N</i>-Dimethylamino-2,3-naphthalimide
  作者：M. Eugenio Vázquez、Juan B. Blanco、B. Imperiali

  DOI：10.1021/ja0449168

  日期：2005.2.1

  We have synthesized a new environment-sensitive fluorophore, 6-N,N-dimethylamino-2,3-naphthalimide (6DMN). This chromophore exhibits valuable fluorescent properties as a biological probe with emission in the 500-600 nm range and a marked response to changes in the environment polarity. The 6DMN fluorescence is red-shifted in polar protic environments, with the maximum emission intensity shifting more than 100 nm from 491 nm in toluene to 592 nm in water. Additionally, the fluorescence quantum yield decreases more than 100-fold from chloroform (Phi = 0.225) to water (Phi = 0.002). The scope and applications of the 6DMN probe are expanded with the synthesis of an Fmoc-protected amino acid derivative (5), which contains the fluorophore. This unnatural amino acid has been introduced into several peptides, demonstrating that it can be manipulated under standard solid-phase peptide synthesis conditions. Peptides incorporating the new residue can be implemented for monitoring protein-protein interactions as exemplified in studies with Sire homology 2 (SH2) phosphotyrosine binding domains. The designed peptides exhibit a significant increase in the quantum yield of the long wavelength fluorescence emission band (596 nm) upon binding to selected SH2 domains (e.g., Crk SH2, Abl SH2, and PI3K SH2). The peptides can be used as ratiometric sensors, since the short wavelength band (460 nm) was found almost invariable throughout the titrations.