allyl (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-aminopropanoate | 755759-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-aminopropanoate
• 英文别名: prop-2-enyl (2S)-3-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 755759-84-3
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: CUYYXORZNFUMEU-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-aminopropanoate 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 14.0h， 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
• 作为产物：
  描述：

  在 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 2.5h， 生成 allyl (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-aminopropanoate
  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

• 4‐Aminophthalimide Amino Acids as Small and Environment‐Sensitive Fluorescent Probes for Transmembrane Peptides
  作者：Samantha Wörner、Franziska Rönicke、Anne S. Ulrich、Hans‐Achim Wagenknecht

  DOI：10.1002/cbic.201900520

  日期：2020.3.2

  factor receptor. It was possible to distinguish their locations, either in the hydrophobic core of the lipid bilayer or at the membrane surface, by fluorescence readout, including blue shift and increased quantum yield. An important feature is the small size of the 4-aminophthalimide chromophore. It makes one of the new amino acids approximately isosteric to tryptophan, typically used as a very small

  需要对跨膜 (TM) 肽进行荧光探测来补充最先进的方法（主要是定向圆二色性和固态核磁共振光谱），并允许在活细胞中成像。合成了三种在其侧链中结合了溶剂化荧光 4-氨基邻苯二甲酰亚胺的新氨基酸，以检查人表皮生长因子受体的 α-螺旋 TM 片段的局部极性。通过荧光读数（包括蓝移和增加的量子产率）可以区分它们的位置，无论是在脂质双层的疏水核心还是在膜表面。一个重要特征是 4-氨基邻苯二甲酰亚胺发色团尺寸小。它使一种新氨基酸与色氨酸大致等排，通常用作肽和蛋白质中的非常小的荧光氨基酸。与色氨酸中唯一的弱荧光吲哚系统相比，4-氨基邻苯二甲酰亚胺部分产生信息量明显更多的荧光读数，并且在生物聚合物吸收范围之外被选择性激发。
• A new environment-sensitive fluorescent amino acid for Fmoc-based solid phase peptide synthesis
  作者：M. Eugenio Vázquez、Deborah M. Rothman、Barbara Imperiali

  DOI：10.1039/b408001g

  日期：——

  A new 4-(N,N-dimethylamino) phthalimide-based environment-sensitive fluorescent building block for solid phase peptide synthesis 3, has been synthesized and incorporated into peptides. Peptides incorporating this residue show great potential for biological applications in sensing protein/protein interactions.

  一种新的基于 4-(N,N-二甲基氨基)邻苯二甲酰亚胺的环境敏感型荧光构件 3 已被合成并加入肽中。含有该残基的肽在感知蛋白质/蛋白质相互作用的生物学应用中显示出巨大的潜力。
• Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligo-dipeptides Tagged with Orotic Acid Derivatives as Recognition Elements
  作者：Xuejun Zhang、Ramanarayanan Krishnamurthy

  DOI：10.1002/anie.200904188

  日期：2009.10.12

  Base‐pairing properties of oligo‐dipeptides tagged with orotic acid and its 2,4‐diamino counterpart (see structure) are found to be consistent with previously observed correlations between ΔpKa values and the pairing strength of complementary bases. The combined results provide a general justification for anticipating the base‐pairing propensity of a recognition element based on its pKa value and the pH

  合作起来！低聚二肽的碱基配对性质具有标记乳清酸和它的2,4-二氨基对应物（见结构）被发现与ΔP之间先前观察到的相关性一致ķ一个 值和互补的碱基配对强度。合并的结果为基于识别元件的p K a 值和介质的pH值预测识别元件的碱基配对倾向提供了一般的依据。
• 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