(S)-2-amino-N-((S)-1-(hex-5-yn-1-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methylpentanamide | 1374647-08-1

• 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
• 英文名称: (S)-2-amino-N-((S)-1-(hex-5-yn-1-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methylpentanamide
• CAS: 1374647-08-1
• 化学式: C₂₁H₃₁N₃O₂
• 分子量: 357.496
• InChiKey: RNDQQYLUTGTYRJ-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  84.22
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-((S)-1-(hex-5-yn-1-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methylpentanamide 、 (2R,4R,5S)-5-(4-benzoylbenzamido)-2-benzyl-4-((tert-butyldimethylsilyl)oxy)-6-phenylhexanoic acid 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， 以91%的产率得到4-benzoyl-N-((2S,3R,5R)-5-benzyl-3-((tert-butyldimethylsilyl)oxy)-6-(((S)-1-(((S)-1-(hex-5-yn-1-ylamino)-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-6-oxo-1-phenylhexan-2-yl)benzamide
  参考文献：
  名称：

  Development of clickable active site-directed photoaffinity probes for γ-secretase

  摘要：

  We have developed clickable active site-directed photoaffinity probes for gamma-secretase which incorporate a photoreactive benzophenone group and an alkyne handle for subsequent click chemistry mediated conjugation with azide-linked reporter tags for visualization (e.g., TAMRA-azide) or enrichment (e.g., biotinazide) of labeled proteins. Specifically, we synthesized clickable analogs of L646 (2) and L505 (3) and validated specific labeling to presenilin-1 N-terminal fragment (PS1-NTF), the active site aspartyl protease component within the gamma-secretase complex. Additionally, we were able to identify signal peptide peptidase (SPP) by Western blot analysis. Furthermore, we analyzed the photo-labeled proteins in an unbiased fashion by click chemistry with TAMRA-azide followed by in-gel fluorescence detection. This approach expands the utility of gamma-secretase inhibitor (GSI) photoaffinity probes in that labeled proteins can be tagged with any number of azide-linked reporters groups using a single clickable photoaffinity probe for target pull down and/or fluorescent imaging applications. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.027
• 作为产物：
  描述：

  N-(5-己炔基)酞酰亚胺 在 HATU 、 N,N-二异丙基乙胺 、 三氟乙酸 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-amino-N-((S)-1-(hex-5-yn-1-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methylpentanamide
  参考文献：
  名称：

  Development of clickable active site-directed photoaffinity probes for γ-secretase

  摘要：

  We have developed clickable active site-directed photoaffinity probes for gamma-secretase which incorporate a photoreactive benzophenone group and an alkyne handle for subsequent click chemistry mediated conjugation with azide-linked reporter tags for visualization (e.g., TAMRA-azide) or enrichment (e.g., biotinazide) of labeled proteins. Specifically, we synthesized clickable analogs of L646 (2) and L505 (3) and validated specific labeling to presenilin-1 N-terminal fragment (PS1-NTF), the active site aspartyl protease component within the gamma-secretase complex. Additionally, we were able to identify signal peptide peptidase (SPP) by Western blot analysis. Furthermore, we analyzed the photo-labeled proteins in an unbiased fashion by click chemistry with TAMRA-azide followed by in-gel fluorescence detection. This approach expands the utility of gamma-secretase inhibitor (GSI) photoaffinity probes in that labeled proteins can be tagged with any number of azide-linked reporters groups using a single clickable photoaffinity probe for target pull down and/or fluorescent imaging applications. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.027