((4-(4-Amino-phenylazo)-phenylcarbamoyl)-methyl)-carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: ((4-(4-Amino-phenylazo)-phenylcarbamoyl)-methyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[4-[(4-aminophenyl)diazenyl]anilino]-2-oxoethyl]carbamate
• 化学式: C₁₉H₂₃N₅O₃
• 分子量: 369.423
• InChiKey: KVLGZJDJHDXYCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((4-(4-Amino-phenylazo)-phenylcarbamoyl)-methyl)-carbamic acid tert-butyl ester 在 三乙胺 、 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 20.0h， 生成
  参考文献：
  名称：

  Design of a Highly Bistable Photoswitchable Tethered Ligand for Rapid and Sustained Manipulation of Neurotransmission

  摘要：

  Photoswitchable neurotransmitter receptors are powerful tools for precise manipulation of neural signaling. However, their applications for slow or long-lasting biological events are constrained by fast thermal relaxation of cis-azobenzene. We address this issue by modifying the ortho positions of azobenzene used in the tethered ligand. In cultured cells and intact brain tissue, conjugating inhibitory neurotransmitter receptors with one of the derivatives, dMPC1, allows bidirectional receptor control with 380 and 500 nm light. Moreover, the receptors can be locked in either an active or an inactive state in darkness after a brief pulse of light. This strategy thus enables both rapid and sustained manipulation of neurotransmission, allowing optogenetic interrogation of neural functions over a broad range of time scales.

  DOI：

  10.1021/jacs.8b03942
• 作为产物：
  描述：

  BOC-甘氨酸 、 对二氨基偶氮苯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以66%的产率得到((4-(4-Amino-phenylazo)-phenylcarbamoyl)-methyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Photoreactive regulator of protein function and methods of use thereof

  摘要：

  本发明提供了一种合成蛋白功能调节剂，该调节剂是一种光敏调节剂。本发明还提供了一种包括所述合成调节剂的光调节多肽。还提供了包括所述光调节多肽的细胞和膜。本发明还提供了一种通过使用光来调节蛋白功能的方法。本发明还提供了一种识别调节蛋白功能的药剂的方法。

  公开号：

  US09097707B2

文献信息

• Photoreactive regulator of protein function and methods of use thereof
  申请人：The Regents of the University of California

  公开号：US09097707B2

  公开（公告）日：2015-08-04

  The present invention provides a synthetic regulator of protein function, which regulator is a light-sensitive regulator. The present invention further provides a light-regulated polypeptide that includes a subject synthetic regulator. Also provided are cells and membranes comprising a subject light-regulated polypeptide. The present invention further provides methods of modulating protein function, involving use of light. The present invention further provides methods of identifying agents that modulate protein function.

  本发明提供了一种合成蛋白功能调节剂，该调节剂是一种光敏调节剂。本发明还提供了一种包括所述合成调节剂的光调节多肽。还提供了包括所述光调节多肽的细胞和膜。本发明还提供了一种通过使用光来调节蛋白功能的方法。本发明还提供了一种识别调节蛋白功能的药剂的方法。
• Design of a Highly Bistable Photoswitchable Tethered Ligand for Rapid and Sustained Manipulation of Neurotransmission
  作者：Wan-Chen Lin、Ming-Chi Tsai、Rajit Rajappa、Richard H. Kramer

  DOI：10.1021/jacs.8b03942

  日期：2018.6.20

  Photoswitchable neurotransmitter receptors are powerful tools for precise manipulation of neural signaling. However, their applications for slow or long-lasting biological events are constrained by fast thermal relaxation of cis-azobenzene. We address this issue by modifying the ortho positions of azobenzene used in the tethered ligand. In cultured cells and intact brain tissue, conjugating inhibitory neurotransmitter receptors with one of the derivatives, dMPC1, allows bidirectional receptor control with 380 and 500 nm light. Moreover, the receptors can be locked in either an active or an inactive state in darkness after a brief pulse of light. This strategy thus enables both rapid and sustained manipulation of neurotransmission, allowing optogenetic interrogation of neural functions over a broad range of time scales.