N-[芴甲氧羰基]-N-甲基-L-色氨酸 | 112913-63-0

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-[芴甲氧羰基]-N-甲基-L-色氨酸
• 英文名称: Fmoc-Nalpha-methyl-L-tryptophan
• 英文别名: (2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 112913-63-0
• 化学式: C₂₇H₂₄N₂O₄
• 分子量: 440.499
• InChiKey: IYEODAZATZJQGN-VWLOTQADSA-N

物化性质

• 沸点：
  683.3±55.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[[(2S,3S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopentan-2-yl]carbamoylamino]hexanoate 、 N-[芴甲氧羰基]-N-甲基-L-色氨酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 brunsvicamide A
  参考文献：
  名称：

  Solid-Support Based Total Synthesis and Stereochemical Correction of Brunsvicamide A

  摘要：

  A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected D-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.

  DOI：

  10.1021/ol801064d
• 作为产物：
  描述：

  甲醇 、 氯甲酸-9-芴基甲酯 、 L-色氨酸 生成 N-[芴甲氧羰基]-N-甲基-L-色氨酸
  参考文献：
  名称：

  Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis

  摘要：

  N-Methyl amino acids and their Fmoc derivatives are synthesized in high yield and purity on solid support using the Fukuyama amine synthesis protocol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01774-7

文献信息

• Comparison of backbone modification in protein β-sheets by α→γ residue replacement and α-residue methylation
  作者：George A. Lengyel、Zachary E. Reinert、Brian D. Griffith、W. Seth Horne

  DOI：10.1039/c4ob00886c

  日期：——

  The mimicry of protein tertiary structure by oligomers with unnatural backbones is a significant contemporary research challenge. Among common elements of secondary structure found in natural proteins, sheets have proven the most difficult to address. Here, we report the systematic comparison of different strategies for peptide backbone modification in β-sheets with the goal of identifying the best method for replacing a multi-stranded sheet in a protein tertiary fold. The most effective sheet modifications examined led to native-like tertiary folding behavior with a thermodynamic folded stability comparable to the prototype protein on which the modified backbones are based.

  通过不自然骨架的聚合物模拟蛋白质三级结构是当今一个重要的研究挑战。在天然蛋白质中常见的次级结构元素中，层析结构被证明是最难处理的。在这里，我们报告了不同策略进行肽骨架改造以形成β-层的系统比较，目的是确定替换蛋白质三级折叠中的多股层的最佳方法。所检查的最有效的层析改造导致了类似本征的三级折叠行为，其热力学折叠稳定性与所基于的原型蛋白相当。
• [EN] FLUORESCENTLY LABELED MOLECULES CONTAINING MODIFIED TRYPTOPHAN<br/>[FR] MOLÉCULES MARQUÉES PAR FLUORESCENCE CONTENANT DU TRYPTOPHANE MODIFIÉ
  申请人：SEED RES AND DEV LLC

  公开号：WO2016133913A1

  公开（公告）日：2016-08-25

  The present disclosure relates to new fluorescent molecules that contain N-alkylated or N-acylated tryptophan and do not substantially quench fluorescent labels attached to the molecules, and the use of such molecules in preparing and studying various compounds, such as substrates and inhibitors for assays of enzymes (e.g., caspases, such as caspase-1 which is an important enzyme in inflammation). An enzyme substrate or enzyme inhibitor that contains a modified tryptophan and fluorescent label as disclosed herein can be studied without loss of signal by Förster quenching. By reducing or eliminating this quenching, more useful labeled molecules with improved properties for assay development can be prepared.

  本公开涉及含有N-烷基化或N-酰化色氨酸的新荧光分子，这些分子不会显着猝灭连接到分子上的荧光标记，并且利用这些分子在制备和研究各种化合物（例如用于酶（如半胱氨酸蛋白酶，如炎症中的重要酶半胱氨酸蛋白酶-1）的测定的底物和抑制剂）中的应用。根据本公开的含有经修改的色氨酸和荧光标记的酶底物或酶抑制剂可以通过Förster猝灭进行研究，而不会丢失信号。通过减少或消除这种猝灭作用，可以制备更有用的带标记分子，具有改进的性质用于测定方法的开发。
• NEUROPEPTIDE ANALOGS, COMPOSITIONS, AND METHODS FOR TREATING PAIN
  申请人：NeuroAdjuvants, Inc.

  公开号：US20170020951A1

  公开（公告）日：2017-01-26

  Neuropeptide analogs and compositions including neuropeptide analogs are described herein. Also provided are methods of producing and using the neuropeptide analogs and compositions including one or more neuropeptide analogs.

  本文描述了神经肽类似物和包括神经肽类似物的组合物。还提供了生产和使用神经肽类似物和包括一个或多个神经肽类似物的方法。
• MACROCYCLIC COMPOUNDS FOR INHIBITION OF TUMOR NECROSIS FACTOR ALPHA
  申请人：Lee Jinbo

  公开号：US20100152099A1

  公开（公告）日：2010-06-17

  The invention provides macrocyclic compounds and methods for their synthesis and use. In particular, the invention provides macrocyclic compounds that modulate the activity of tumor necrosis factor alpha and/or are useful in the treatment of medical conditions, such as, rheumatoid arthritis, psoriasis, and asthma.

  该发明提供了大环化合物及其合成和使用方法。具体而言，该发明提供了调节肿瘤坏死因子α活性和/或用于治疗医学状况（如类风湿性关节炎、银屑病和哮喘）的大环化合物。
• Neuropeptide analogs, compositions, and methods for treating pain
  申请人：NeuroAdjuvants, Inc.

  公开号：US10172909B2

  公开（公告）日：2019-01-08

  Neuropeptide analogs and compositions including neuropeptide analogs are described herein. Also provided are methods of producing and using the neuropeptide analogs and compositions including one or more neuropeptide analogs.

  本文描述了神经肽类似物和包括神经肽类似物的组合物。还提供了生产和使用神经肽类似物和包括一种或多种神经肽类似物的组合物的方法。