4-benzoyl-N-[(2S,3R,5R)-5-benzyl-6-[[(2S)-1-[[(2S)-1-(hex-5-ynylamino)-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-6-oxo-1-phenylhexan-2-yl]benzamide | 1374647-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 4-benzoyl-N-[(2S,3R,5R)-5-benzyl-6-[[(2S)-1-[[(2S)-1-(hex-5-ynylamino)-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-6-oxo-1-phenylhexan-2-yl]benzamide
• CAS: 1374647-06-9
• 化学式: C₅₄H₆₀N₄O₆
• 分子量: 861.094
• InChiKey: BFCGFUNQWHAMEE-YKORCUBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  64
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-苯甲酰苯甲酸 在 咪唑 、 四丁基氟化铵 、 水 、 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 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-benzoyl-N-[(2S,3R,5R)-5-benzyl-6-[[(2S)-1-[[(2S)-1-(hex-5-ynylamino)-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-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

文献信息

• Development of clickable active site-directed photoaffinity probes for γ-secretase
  作者：Christina J. Crump、Christopher W. am Ende、T. Eric Ballard、Nikolay Pozdnyakov、Martin Pettersson、De-Ming Chau、Kelly R. Bales、Yue-Ming Li、Douglas S. Johnson

  DOI：10.1016/j.bmcl.2012.02.027

  日期：2012.4

  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.