(S)-N-((S)-20-amino-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)-2-(2-chloroacetamido)propanamide | 1235572-60-7

• 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
• 英文名称: (S)-N-((S)-20-amino-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)-2-(2-chloroacetamido)propanamide
• CAS: 1235572-60-7
• 化学式: C₈₄H₉₇ClN₁₈O₁₀
• 分子量: 1554.26
• InChiKey: MZIFSYDDEHDIQS-OAJMSYQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  113.0
• 可旋转键数：
  48.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  355.75
• 氢给体数：
  8.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  (S)-N-((S)-20-amino-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)-2-(2-chloroacetamido)propanamide 、 (+)生物素-N-琥珀酰亚胺基酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以40%的产率得到N-((4S,13S)-4,13-bis(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)-4-hydroxybenzyl)-1-chloro-2,5,8,11,14-pentaoxo-18,21,24-trioxa-3,6,9,12,15-pentaazahexacosan-26-yl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide
  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：

  (S)-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)-2-(2-chloroacetamido)propanamide 在 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 (S)-N-((S)-20-amino-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)-2-(2-chloroacetamido)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