(1-[(9H-芴-9-甲氧基羰基氨基)-甲基]-环己基)-乙酸 | 882847-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (1-[(9H-芴-9-甲氧基羰基氨基)-甲基]-环己基)-乙酸
• 中文别名: FMOC-加巴喷丁
• 英文名称: Fmoc-gabapentin
• 英文别名: 2-[1-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]cyclohexyl]acetic acid
• CAS: 882847-19-0
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: JQJOWILVGOJWJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  (1-[(9H-芴-9-甲氧基羰基氨基)-甲基]-环己基)-乙酸 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  通过立体选择性氟化控制γ-肽的螺旋度

  摘要：

  扭转一下：CF键已经通过立体控制结合到γ-六肽的骨架上。取决于立体化学构型，氟的存在可以稳定或破坏螺旋构象。氟还设定了螺旋的“惯性”。

  DOI：

  10.1002/ejoc.202001619
• 作为产物：
  描述：

  加巴喷丁 、 9-芴基甲基1-苯并三唑基碳酸酯 在 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 2.17h， 以2.9 g的产率得到(1-[(9H-芴-9-甲氧基羰基氨基)-甲基]-环己基)-乙酸
  参考文献：
  名称：

  An improved synthesis of a fluorescent gabapentin–choline conjugate for single molecule detection

  摘要：

  Voltage-gated calcium ion channels comprise pore-forming alpha(1) and auxiliary alpha(2)delta, beta, and gamma subunits. They are important molecular devices involved in a variety of cell functions. Fluorescently labeled acylcholine analogues are important in studies such as ion channel regulation. Cy3-3-acetylcholine has recently been synthesized for single molecule detection studies; albeit in an extremely low overall yield (0.06%). In this Work, an alternative route to that used in the previous Cy3-3-acetylcholine synthesis was developed with a 90% yield at a significantly lower material cost. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.02.125

文献信息

• Divergent, C–C Bond Forming Macrocyclizations Using Modular Sulfonylhydrazone and Derived Substrates
  作者：Wenqing Xu、Lauren E. Brown、John A. Porco

  DOI：10.1021/acs.joc.1c01848

  日期：2021.12.3

  forming macrocycle construction is described. Modular sulfonylhydrazone and derived pyridotriazole substrates with three key building blocks have been constructed and cyclized to afford diverse macrocyclic frameworks. Broad substrate scope and functional group tolerance have been demonstrated. In addition, site-selective postfunctionalization allowed for further diversification of macrocyclic cores.

  描述了形成 C-C 键的大环结构的不同方法。具有三个关键结构单元的模块化磺酰腙和衍生的吡啶并三唑底物已被构建并环化以提供不同的大环框架。广泛的底物范围和官能团耐受性已被证明。此外，位点选择性后官能化允许大环核的进一步多样化。
• The influence of backbone fluorination on the helicity of α/γ-hybrid peptides
  作者：Alpesh Ramanlal Patel、Aggie Lawer、Mohan Bhadbhade、Luke Hunter

  DOI：10.1039/d3ob02016a

  日期：2024.2.21

  from this conformation in a controlled way. Herein, we explore stereoselective fluorination as a method for controlling the conformations of α/γ-hybrid peptides. We show through a combination of X-ray, NMR and CD analyses that fluorination can either stabilize or disrupt the 12-helix, depending on the fluorine stereochemistry. These findings could inform the ongoing development of diverse functional hybrid

  由 α- 和 γ- 氨基酸交替模式组成的肽作为抗代谢生物活性剂具有潜在的价值。为了获得最佳功能，通常需要某种构象限制来稳定主要的 12 螺旋，或者以受控方式将肽从该构象转移。在此，我们探索立体选择性氟化作为控制 α/γ-杂合肽构象的方法。我们通过结合 X 射线、NMR 和 CD 分析表明，氟化可以稳定或破坏 12 螺旋，具体取决于氟的立体化学。这些发现可以为多种功能杂合肽的持续开发提供信息。
• An improved synthesis of a fluorescent gabapentin–choline conjugate for single molecule detection
  作者：Haitao Wu、Gurpreet Kaur、Gary L. Griffiths

  DOI：10.1016/j.tetlet.2009.02.125

  日期：2009.5

  Voltage-gated calcium ion channels comprise pore-forming alpha(1) and auxiliary alpha(2)delta, beta, and gamma subunits. They are important molecular devices involved in a variety of cell functions. Fluorescently labeled acylcholine analogues are important in studies such as ion channel regulation. Cy3-3-acetylcholine has recently been synthesized for single molecule detection studies; albeit in an extremely low overall yield (0.06%). In this Work, an alternative route to that used in the previous Cy3-3-acetylcholine synthesis was developed with a 90% yield at a significantly lower material cost. Published by Elsevier Ltd.
• Controlling γ‐Peptide Helicity with Stereoselective Fluorination
  作者：Aggie Lawer、Luke Hunter

  DOI：10.1002/ejoc.202001619

  日期：2021.2.19

  Do the twist: C−F bonds have been incorporated, with stereocontrol, onto the backbone of a γ‐hexapeptide. The presence of fluorine either stabilizes or disrupts the helical conformation, depending on the stereochemical configuration. Fluorine also sets the “handedness” of the helix.

  扭转一下：CF键已经通过立体控制结合到γ-六肽的骨架上。取决于立体化学构型，氟的存在可以稳定或破坏螺旋构象。氟还设定了螺旋的“惯性”。