tert-butyl (4S)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate | 792867-52-8

• 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: tert-butyl (4S)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate
• CAS: 792867-52-8
• 化学式: C₁₂H₂₃N₃O₄
• 分子量: 273.332
• InChiKey: DGGXMGOWINJHNE-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate 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 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (4S)-4-[[(2S)-2-[[(2R)-2-[[(4aR,6R,7R,8R,8aS)-7-acetamido-6-(10-azidodecoxy)-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
  参考文献：
  名称：

  An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction

  摘要：

  Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, an efficient fluorescent labeling strategy is developed generally for bioactive natural products. Essentials of a successful labeling include the personalized introduction of an azido functionality to specific targets by a selective and efficient manner, and the strategic adjustment of reaction sequence to avoid possible side reactions under the 'click' reaction conditions. Such a protocol has been successfully applied to the fluorescent labeling of four bioactive small molecules in different chemical categories in this study. Advantages of this labeling protocol include the use of inexpensive reagents, ease of operation, free-of-protections at the 'click' step, and suiting a wide range of bioactive molecules bearing the reactive functionalities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.069
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到tert-butyl (4S)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate
  参考文献：
  名称：

  An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction

  摘要：

  Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, an efficient fluorescent labeling strategy is developed generally for bioactive natural products. Essentials of a successful labeling include the personalized introduction of an azido functionality to specific targets by a selective and efficient manner, and the strategic adjustment of reaction sequence to avoid possible side reactions under the 'click' reaction conditions. Such a protocol has been successfully applied to the fluorescent labeling of four bioactive small molecules in different chemical categories in this study. Advantages of this labeling protocol include the use of inexpensive reagents, ease of operation, free-of-protections at the 'click' step, and suiting a wide range of bioactive molecules bearing the reactive functionalities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.069

文献信息

• An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction
  作者：Yan-Hong Zhang、Zheng-Xi Gao、Chun-Long Zhong、Hai-Bin Zhou、Lei Chen、Wen-Min Wu、Xin-Jun Peng、Zhu-Jun Yao

  DOI：10.1016/j.tet.2007.04.069

  日期：2007.7

  Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, an efficient fluorescent labeling strategy is developed generally for bioactive natural products. Essentials of a successful labeling include the personalized introduction of an azido functionality to specific targets by a selective and efficient manner, and the strategic adjustment of reaction sequence to avoid possible side reactions under the 'click' reaction conditions. Such a protocol has been successfully applied to the fluorescent labeling of four bioactive small molecules in different chemical categories in this study. Advantages of this labeling protocol include the use of inexpensive reagents, ease of operation, free-of-protections at the 'click' step, and suiting a wide range of bioactive molecules bearing the reactive functionalities. (c) 2007 Elsevier Ltd. All rights reserved.