N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionic acid | 845255-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionic acid
• 英文别名: 9-Fluorenylmethoxycarbonyl-[6-N,N-dimethylamino-2,3-napthalimido]-alanine；(2S)-3-[6-(dimethylamino)-1,3-dioxobenzo[f]isoindol-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 845255-75-6
• 化学式: C₃₂H₂₇N₃O₆
• 分子量: 549.583
• InChiKey: JDUWKFAMJVKCDF-NDEPHWFRSA-N

物化性质

• 沸点：
  815.9±65.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-O-叔丁基-L-谷氨酸 、 Fmoc-L-异亮氨酸 、 N-芴甲氧羰基-O-苄基-L-磷酸酪氨酸 、 N-α-Fmoc-N-β-[6-dimethylamino-2,3-naphthalimido]-L-diaminopropionic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 Ac-Glu-Dap(6-N,N-dimethylamino-2,3-naphthalimide)-Gly-phosphotyrosine-Asp-His-Pro-Asn-Ile-(CONH2)
  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 四(三苯基膦)钯 、 苯硅烷 、 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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 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

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。
• 6-<i>N,N</i>-Dimethylamino-2,3-naphthalimide:  A New Environment-Sensitive Fluorescent Probe in δ- and μ-Selective Opioid Peptides
  作者：M. Eugenio Vázquez、Juan B. Blanco、Severo Salvadori、Claudio Trapella、Roberto Argazzi、Sharon D. Bryant、Yunden Jinsmaa、Lawrence H. Lazarus、Lucia Negri、Elisa Giannini、Roberta Lattanzi、Mariantonella Colucci、Gianfranco Balboni

  DOI：10.1021/jm060343t

  日期：2006.6.1

  new environment-sensitive fluorophore, 6-N,N-(dimethylamino)-2,3-naphthalimide (6DMN) was introduced in the delta-selective opioid peptide agonist H-Dmt-Tic-Glu-NH2 and in the mu-selective opioid peptide agonist endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2). Environment-sensitive fluorophores are a special class of chromophores that generally exhibit a low quantum yield in aqueous solution but become highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. New fluorescent delta-selective irreversible antagonists (H-Dmt-Tic-Glu-NH-(CH2)(5)-CO-Dap(6DMN)-NH2 (1) and H-Dmt-Tic-Glu-Dap(6DMN)-NH2 ( 2)) were identified as potential fluorescent probes showing good properties for use in studies of distribution and internalization of delta receptors by confocal laser scanning microscopy.
• 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.