N-芴甲氧羰基DMNB-L-丝氨酸 | 628280-43-3

• 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DMNB-L-丝氨酸
• 英文名称: N-(9-Fluorenylmethyloxycarbonyl)-O-(4,5-dimethoxy-2-nitrobenzyl)-L-serine
• 英文别名: N-Fmoc DMNB-L-serine；(2S)-3-[(4,5-dimethoxy-2-nitrophenyl)methoxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 628280-43-3
• 化学式: C₂₇H₂₆N₂O₉
• 分子量: 522.511
• InChiKey: GEIDGZJCBUYWDB-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基DMNB-L-丝氨酸 在 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 o-(4,5-Dimethoxy-2-nitrobenzyl)-L-serine
  参考文献：
  名称：

  A Light-Activated Probe of Intracellular Protein Kinase Activity

  摘要：

  The first example of a photoactivated probe of intracellular enzymatic activity is described. The caged derivative of a fluorescent protein kinase C peptide-based sensor was prepared by modifying the free hydroxyl group of a phosphorylatable serine moiety with a photolabile appendage that blocks phosphoryl transfer. We have demonstrated that the caged sensor allows one to (1) sample PKC activity with exquisite temporal precision, (2) control the relative amount of active sensor available for phosphorylation, and (3) examine protein kinase activity at multiple time points.

  DOI：

  10.1021/ja037801x
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester 在 N-甲基吗啉 、 四(三苯基膦)钯 、 三氟甲磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 N-芴甲氧羰基DMNB-L-丝氨酸
  参考文献：
  名称：

  A Light-Activated Probe of Intracellular Protein Kinase Activity

  摘要：

  The first example of a photoactivated probe of intracellular enzymatic activity is described. The caged derivative of a fluorescent protein kinase C peptide-based sensor was prepared by modifying the free hydroxyl group of a phosphorylatable serine moiety with a photolabile appendage that blocks phosphoryl transfer. We have demonstrated that the caged sensor allows one to (1) sample PKC activity with exquisite temporal precision, (2) control the relative amount of active sensor available for phosphorylation, and (3) examine protein kinase activity at multiple time points.

  DOI：

  10.1021/ja037801x

文献信息

• An Integrated Chemical Cytometry Method: Shining a Light on Akt Activity in Single Cells
  作者：Emilie R. Mainz、Qunzhao Wang、David S. Lawrence、Nancy L. Allbritton

  DOI：10.1002/anie.201606914

  日期：2016.10.10

  light‐programmable, cell‐permeable reporter deliverable simultaneously to many cells. The reporter's ability to act as a substrate for Akt, a key oncogenic kinase, was masked by a 2‐4,5‐dimethoxy 2‐nitrobenzyl (DMNB) moiety. Upon exposure to ultraviolet light and release of the masking moiety, the substrate sequence enabled programmable reaction times within the cell cytoplasm. When coupled to automated single‐cell

  评估小型临床样品中致癌激酶活性的工具具有指导肿瘤学精密医学的能力。现有平台已经证明了对蛋白激酶活性的深刻见解，但是这些技术不适合研究大量原代人细胞中的激酶行为。为了解决这些局限性，我们开发了一种集成分析系统，该系统利用可同时传输到许多细胞的光可编程，可渗透细胞的报告分子。报道者充当关键致癌激酶Akt的底物的能力被2-4,5-二甲氧基2-硝基苄基（DMNB）部分掩盖。暴露于紫外线并释放掩蔽部分后，底物序列可实现细胞质内可编程的反应时间。
• Long-Wavelength Fluorescent Reporters for Monitoring Protein Kinase Activity
  作者：Nathan P. Oien、Luong T. Nguyen、Finith E. Jernigan、Melanie A. Priestman、David S. Lawrence

  DOI：10.1002/anie.201309691

  日期：2014.4.7

  obscures subcellular monitoring at wavelengths less than 600 nm. To address this, tunable fluorescent reporters for protein kinase activity were developed. The probing wavelength is preprogrammed by using readily available fluorophores, thereby enabling detection within the optical window of tissue, specifically in the far‐red and near‐IR region. These agents were used to monitor endogenous cAMP‐dependent

  体内光学成像必须克服组织光学窗口 (600–1000 nm) 的限制。尽管有多种荧光团可以在光谱的红色和近红外区域可视化，但除蛋白酶外，酶的长波长探针很少。这种情况对研究红细胞的细胞内生物化学提出了特殊的挑战，红细胞的高血红蛋白含量在小于 600 nm 的波长下光学掩盖了亚细胞监测。为了解决这个问题，开发了用于蛋白激酶活性的可调荧光报告基因。探测波长通过使用现成的荧光团进行预编程，从而能够在组织的光学窗口内进行检测，特别是在远红外和近红外区域。
• Fluorescent assays for protein kinases
  申请人：Lawrence S. David

  公开号：US20050054024A1

  公开（公告）日：2005-03-10

  This invention provides fluorescently-labeled peptide substrates for protein kinases; methods using the substrates for identifying compounds that inhibit protein kinases, for determining if particular protein kinases are active in cells, for diagnosing diseases, and for preparing compositions; and compositions comprising the substrates.

  本发明提供了荧光标记的肽底物，用于蛋白激酶；使用这些底物的方法，用于识别抑制蛋白激酶的化合物，确定细胞中特定的蛋白激酶是否活跃，诊断疾病以及制备组成物；以及包含这些底物的组成物。
• US7759459B2
  申请人：——

  公开号：US7759459B2

  公开（公告）日：2010-07-20