| 1235572-56-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 1235572-56-1
• 化学式: C₈₇H₁₀₂N₂₀O₁₁
• 分子量: 1603.89
• InChiKey: WGSHTPZIRKDKNF-HFYKEEGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  118.0
• 可旋转键数：
  48.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  387.72
• 氢给体数：
  7.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(S)-2-amino-N-((S)-20-azido-7-(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)-4-hydroxybenzyl)-2,5,8-trioxo-12,15,18-trioxa-3,6,9-triazaicosyl)-3-(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)-4-hydroxyphenyl)propanamide
  参考文献：
  名称：

  Selective Covalent Labeling of Tag-Fused GPCR Proteins on Live Cell Surface with a Synthetic Probe for Their Functional Analysis

  摘要：

  Selective protein labeling with a small molecular probe is a versatile method for elucidating protein functions in living cells. In this paper, we report a covalent labeling method of tag-fused G-protein coupled receptor (GPCR) proteins expressing on cell surfaces utilizing small functional molecules. This method employs the selective and rapid reaction of a peptide tag and a molecular probe, which comprises the cysteine-containing short CA6D4x2 tag (CAAAAAADDDDGDDDD) and a tetranuclear Zn(II)-DpaTyr probe containing a reactive alpha-chloroacetyl moiety. The covalent labeling of tag-fused GPCRs such as bradykinin receptor (B2R) and acetylcholine receptor (m1AchR) selectively proceeded under physiological conditions during short incubation (10-30 min) with Zn(II)-DpaTyr probes bearing various functional groups. Labeling with fluorophore-appended Zn(II)-DpaTyr probes enabled visualization of the GPCRs on the surface of HEK293 cells by fluorescence. Labeling with the biotin-appended probe allowed introduction of a biotin unit into the GPCRs. This biotin label was utilized for fluorescence bioimaging studies and postlabeling blotting analysis of the labeled GPCRs by use of the specific biotin-streptavidin interaction. The utility of this labeling method was demonstrated in several function analyses of GPCRs, such as fluorescence visualization of the stimuli-responsive internalization of GPCRs and pH change in endosomes containing the internalized GPCRs.

  DOI：

  10.1021/ja910703v
• 作为产物：
  描述：

  2-[[2-[[(2S)-3-[3,5-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-4-hydroxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetyl]amino]acetic acid 、 (S)-2-amino-N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)-4-hydroxyphenyl)propanamide 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 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以81%的产率得到
  参考文献：
  名称：

  Selective Covalent Labeling of Tag-Fused GPCR Proteins on Live Cell Surface with a Synthetic Probe for Their Functional Analysis

  摘要：

  Selective protein labeling with a small molecular probe is a versatile method for elucidating protein functions in living cells. In this paper, we report a covalent labeling method of tag-fused G-protein coupled receptor (GPCR) proteins expressing on cell surfaces utilizing small functional molecules. This method employs the selective and rapid reaction of a peptide tag and a molecular probe, which comprises the cysteine-containing short CA6D4x2 tag (CAAAAAADDDDGDDDD) and a tetranuclear Zn(II)-DpaTyr probe containing a reactive alpha-chloroacetyl moiety. The covalent labeling of tag-fused GPCRs such as bradykinin receptor (B2R) and acetylcholine receptor (m1AchR) selectively proceeded under physiological conditions during short incubation (10-30 min) with Zn(II)-DpaTyr probes bearing various functional groups. Labeling with fluorophore-appended Zn(II)-DpaTyr probes enabled visualization of the GPCRs on the surface of HEK293 cells by fluorescence. Labeling with the biotin-appended probe allowed introduction of a biotin unit into the GPCRs. This biotin label was utilized for fluorescence bioimaging studies and postlabeling blotting analysis of the labeled GPCRs by use of the specific biotin-streptavidin interaction. The utility of this labeling method was demonstrated in several function analyses of GPCRs, such as fluorescence visualization of the stimuli-responsive internalization of GPCRs and pH change in endosomes containing the internalized GPCRs.

  DOI：

  10.1021/ja910703v