2-(5-(dimethylamino)naphthalene-1-sulfonamido)ethyl 4-methylbenzenesulfonate | 64307-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(5-(dimethylamino)naphthalene-1-sulfonamido)ethyl 4-methylbenzenesulfonate
• 英文别名: N-Dansyl-O-tosylaethanolamin；2-[[5-(Dimethylamino)naphthalen-1-yl]sulfonylamino]ethyl 4-methylbenzenesulfonate
• CAS: 64307-60-4
• 化学式: C₂₁H₂₄N₂O₅S₂
• 分子量: 448.564
• InChiKey: SATCIYLIJMSAPK-UHFFFAOYSA-N

物化性质

• 沸点：
  631.1±65.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(5-(dimethylamino)naphthalene-1-sulfonamido)ethyl 4-methylbenzenesulfonate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 生成 丹磺酰酰胺基乙基硫醇
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  丹酰氯 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-(5-(dimethylamino)naphthalene-1-sulfonamido)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  METHOD FOR PREPARING SITE-SPECIFICALLY MODIFIED PROTEIN BASED ON NOVEL CARBON-CARBON BOND FORMATION

  摘要：

  揭示了一种基于新的碳-碳键形成的方法，用于产生具有特定位点修饰的蛋白质，包括以下三个步骤（标记、激活和偶联步骤）：(a) 通过将特定氨基酸纳入目标蛋白质的选定位置来标记修饰位点；(b) 激活标记的位点；以及(c) 将各种翻译后修饰（PTM）基团或其他化学基团偶联到激活位点，从而获得具有特定位点修饰的蛋白质。用于产生具有特定位点修饰的蛋白质的方法可以通过新的碳-碳键将所需的多样化化学基团，包括翻译后修饰（PTM）基团，纳入目标蛋白质的指定位点。此外，具有特定位点PTM的修饰蛋白质表现出与细胞中存在的目标蛋白质相同的化学和功能特性。因此，本发明对于细胞蛋白质、包括癌症和神经退行性疾病在内的人类疾病的研究以及新药物发现是有用的。

  公开号：

  US20180066011A1

文献信息

• Method for preparing site-specifically modified protein based on novel carbon-carbon bond formation
  申请人：Korea Advanced Institute of Science and Technology

  公开号：US10723760B2

  公开（公告）日：2020-07-28

  A method for producing a site-specifically modified protein based on new carbon-carbon bond formation is disclosed, including the following three steps (marking, activation, and coupling steps): (a) marking of the modification site by incorporating a specific amino acid into a selected position of a target protein; (b) activation of the marked site; and (c) coupling of various post-translational modification (PTM) moieties or other chemical groups onto the activated site to obtain a site-specifically modified protein. The method for producing a site-specifically modified protein can incorporate desired diverse chemical groups including post-translational modification (PTM) moieties into a designated site in a target protein through a new carbon-carbon bond. Furthermore, the modified protein having a site-specific PTM exhibits the same chemical and functional properties as that of a target protein present in cells. Thus, the present invention is useful for studies of cellular proteins, human diseases including cancers and neurodegenerative diseases, and new drug discovery.

  本发明公开了一种基于新碳-碳键形成的位点特异性修饰蛋白质的生产方法，包括以下三个步骤（标记、活化和耦合步骤）：(a) 通过将特定氨基酸加入目标蛋白质的选定位置来标记修饰位点；(b) 激活标记位点；(c) 将各种翻译后修饰（PTM）分子或其他化学基团偶联到激活位点上，以获得位点特异性修饰蛋白质。生产位点特异性修饰蛋白质的方法可以通过新的碳-碳键将所需的各种化学基团（包括翻译后修饰（PTM）分子）结合到目标蛋白质的指定位点上。此外，具有位点特异性 PTM 的修饰蛋白与细胞中的目标蛋白具有相同的化学和功能特性。因此，本发明可用于研究细胞蛋白质、人类疾病（包括癌症和神经退行性疾病）以及新药研发。
• Fluorescent Inhibitors for IspF, an Enzyme in the Non-Mevalonate Pathway for Isoprenoid Biosynthesis and a Potential Target for Antimalarial Therapy
  作者：Christine M. Crane、Johannes Kaiser、Nicola L. Ramsden、Susan Lauw、Felix Rohdich、Wolfgang Eisenreich、William N. Hunter、Adelbert Bacher、François Diederich

  DOI：10.1002/anie.200503003

  日期：2006.2.6
• [EN] NOVEL METHOD FOR PRODUCING PROTEIN HAVING A CARBON-CARBON BOND-BASED SITE-SPECIFIC MODIFICATION<br/>[FR] NOUVEAU PROCÉDÉ DE PRODUCTION DE PROTÉINE AYANT UNE MODIFICATION SPÉCIFIQUE D'UN SITE BASÉE SUR UNE LIAISON CARBONE-CARBONE<br/>[KO] 새로운 탄소-탄소 결합 기반 위치 특이적으로 변형된 단백질의 제조방법
  申请人：KOREA ADVANCED INST SCI & TECH

  公开号：WO2018044130A1

  公开（公告）日：2018-03-08

  본 발명은 특정 위치가 변형된(modified) 목적 단백질의 제조방법에 관한 것으로, 보다 구체적으로는 (a) 목적 단백질의 특정 위치에 아미노산을 첨가하여 변형시킬 위치를 반응기를 가지는 물질로 표지하는 단계; (b) 상기 위치의 표지를 활성화시키는 단계; 및 (c) 상기 활성화된 표지에 번역후변형(post translational modification, PTM) 작용기(moiety)를 부착시켜 변형된 단백질을 수득하는 단계를 포함하는 새로운 탄소-탄소 결합 기반 위치 특이적으로 변형된 목적 단백질의 제조방법에 관한 것이다. 본 발명에 따른 위치 특이적으로 변형된 목적 단백질의 제조 방법은 목적 단백질의 원하는 위치에 원하는 변형(modification)을 추가할 뿐만 아니라, 변형이 추가된 목적 단백질이 세포 내에 존재하는 목적 단백질과 동일한 효과를 나타내어 목적 단백질의 기능연구, 신약 스크리닝에 등에 유용하다.
• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.
• METHOD FOR PREPARING SITE-SPECIFICALLY MODIFIED PROTEIN BASED ON NOVEL CARBON-CARBON BOND FORMATION
  申请人：Korea Advanced Institute of Science and Technology

  公开号：US20180066011A1

  公开（公告）日：2018-03-08

  A method for producing a site-specifically modified protein based on new carbon-carbon bond formation is disclosed, including the following three steps (marking, activation, and coupling steps): (a) marking of the modification site by incorporating a specific amino acid into a selected position of a target protein; (b) activation of the marked site; and (c) coupling of various post-translational modification (PTM) moieties or other chemical groups onto the activated site to obtain a site-specifically modified protein. The method for producing a site-specifically modified protein can incorporate desired diverse chemical groups including post-translational modification (PTM) moieties into a designated site in a target protein through a new carbon-carbon bond. Furthermore, the modified protein having a site-specific PTM exhibits the same chemical and functional properties as that of a target protein present in cells. Thus, the present invention is useful for studies of cellular proteins, human diseases including cancers and neurodegenerative diseases, and new drug discovery.

  揭示了一种基于新的碳-碳键形成的方法，用于产生具有特定位点修饰的蛋白质，包括以下三个步骤（标记、激活和偶联步骤）：(a) 通过将特定氨基酸纳入目标蛋白质的选定位置来标记修饰位点；(b) 激活标记的位点；以及(c) 将各种翻译后修饰（PTM）基团或其他化学基团偶联到激活位点，从而获得具有特定位点修饰的蛋白质。用于产生具有特定位点修饰的蛋白质的方法可以通过新的碳-碳键将所需的多样化化学基团，包括翻译后修饰（PTM）基团，纳入目标蛋白质的指定位点。此外，具有特定位点PTM的修饰蛋白质表现出与细胞中存在的目标蛋白质相同的化学和功能特性。因此，本发明对于细胞蛋白质、包括癌症和神经退行性疾病在内的人类疾病的研究以及新药物发现是有用的。