L458-BPyne | 1374647-07-0

• 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: L458-BPyne
• 英文别名: tert-butyl N-[(2S,3R,5R)-6-[[(2S)-1-[[(2S)-3-(4-benzoylphenyl)-1-(hex-5-ynylamino)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate
• CAS: 1374647-07-0
• 化学式: C₅₂H₆₄N₄O₇
• 分子量: 857.103
• InChiKey: YKCNMCSQOOEJHB-BDHQKZEVSA-N

物化性质

• 沸点：
  1044.6±65.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  63
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(5-己炔基)酞酰亚胺 在 HATU 、 四丁基氟化铵 、 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 、 三氟乙酸 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 L458-BPyne
  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.