benzyl N-[(5S)-6-[[(2S)-1-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-5-(heptanoylamino)-6-oxohexyl]carbamate | 1357344-46-7

• 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: benzyl N-[(5S)-6-[[(2S)-1-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-5-(heptanoylamino)-6-oxohexyl]carbamate
• CAS: 1357344-46-7
• 化学式: C₃₆H₆₁N₃O₇Si
• 分子量: 675.982
• InChiKey: NQQSROMDMOOYIC-ABCZBHHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  47
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl N-[(5S)-6-[[(2S)-1-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-5-(heptanoylamino)-6-oxohexyl]carbamate 在 palladium on activated charcoal 、 氢气 作用下， 生成
  参考文献：
  名称：

  A bright approach to the immunoproteasome: Development of LMP2/β1i-specific imaging probes

  摘要：

  While the constitutive, 26S proteasome plays an important role in regulating many important cellular processes, a variant form known as the immunoproteasome is thought to primarily function in adaptive immune responses. However, recent studies indicate an association of immunoproteasomes with many physiological disorders such as cancer, neurodegenerative, and inflammatory diseases. Despite this, the detailed functions of the immunoproteasome remain poorly understood. Immunoproteasome-specific probes are essential to gain insight into immunoproteasome function. Here, we describe for the first time the development of cell-permeable activity-based fluorescent probes, UK101-Fluor and UK101-B660, which selectively target the catalytically active LMP2/beta 1i subunit of the immunoproteasome. These probes facilitate rapid detection of the cellular localization of catalytically active immunoproteasomes in living cells, providing a valuable tool to analyze immunoproteasome functions. Additionally, as LMP2/beta 1i may serve as a potential tumor biomarker, an LMP2/beta 1i-targeting fluorescent imaging probe may be applicable to a rapid readout assay to determine tumor LMP2/beta 1i levels. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.039
• 作为产物：
  描述：

  、 (2S,4S)-4-amino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1,2-oxiranylheptane 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[(5S)-6-[[(2S)-1-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-5-(heptanoylamino)-6-oxohexyl]carbamate
  参考文献：
  名称：

  A bright approach to the immunoproteasome: Development of LMP2/β1i-specific imaging probes

  摘要：

  While the constitutive, 26S proteasome plays an important role in regulating many important cellular processes, a variant form known as the immunoproteasome is thought to primarily function in adaptive immune responses. However, recent studies indicate an association of immunoproteasomes with many physiological disorders such as cancer, neurodegenerative, and inflammatory diseases. Despite this, the detailed functions of the immunoproteasome remain poorly understood. Immunoproteasome-specific probes are essential to gain insight into immunoproteasome function. Here, we describe for the first time the development of cell-permeable activity-based fluorescent probes, UK101-Fluor and UK101-B660, which selectively target the catalytically active LMP2/beta 1i subunit of the immunoproteasome. These probes facilitate rapid detection of the cellular localization of catalytically active immunoproteasomes in living cells, providing a valuable tool to analyze immunoproteasome functions. Additionally, as LMP2/beta 1i may serve as a potential tumor biomarker, an LMP2/beta 1i-targeting fluorescent imaging probe may be applicable to a rapid readout assay to determine tumor LMP2/beta 1i levels. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.039

文献信息

• A bright approach to the immunoproteasome: Development of LMP2/β1i-specific imaging probes
  作者：Kimberly Cornish Carmony、Do-Min Lee、Ying Wu、Na-Ra Lee、Marie Wehenkel、Jason Lee、Beilei Lei、Chang-Guo Zhan、Kyung-Bo Kim

  DOI：10.1016/j.bmc.2011.06.039

  日期：2012.1

  While the constitutive, 26S proteasome plays an important role in regulating many important cellular processes, a variant form known as the immunoproteasome is thought to primarily function in adaptive immune responses. However, recent studies indicate an association of immunoproteasomes with many physiological disorders such as cancer, neurodegenerative, and inflammatory diseases. Despite this, the detailed functions of the immunoproteasome remain poorly understood. Immunoproteasome-specific probes are essential to gain insight into immunoproteasome function. Here, we describe for the first time the development of cell-permeable activity-based fluorescent probes, UK101-Fluor and UK101-B660, which selectively target the catalytically active LMP2/beta 1i subunit of the immunoproteasome. These probes facilitate rapid detection of the cellular localization of catalytically active immunoproteasomes in living cells, providing a valuable tool to analyze immunoproteasome functions. Additionally, as LMP2/beta 1i may serve as a potential tumor biomarker, an LMP2/beta 1i-targeting fluorescent imaging probe may be applicable to a rapid readout assay to determine tumor LMP2/beta 1i levels. (C) 2011 Elsevier Ltd. All rights reserved.