t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-azido-6'-deoxy-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate | 864070-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-azido-6'-deoxy-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate
• 英文别名: tert-butyl (Z)-2-[(2S,3R,4R,5R,6R)-6-(azidomethyl)-3-(1,3-dioxoisoindol-2-yl)-4,5-dihydroxyoxan-2-yl]oxy-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 864070-77-9
• 化学式: C₂₇H₂₈N₄O₉
• 分子量: 552.541
• InChiKey: CCAJLZOFOOAMQC-ZSMJMNQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-azido-6'-deoxy-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate 在 Lindlar's catalyst 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-[N-(N-(N-(biotinyl)glycyl)glycyl)glycyl]-amino-6'-deoxy-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate
  参考文献：
  名称：

  Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes

  摘要：

  Circadian rhythmic plant leaf-movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We revealed that specific binding proteins (210 and 180 kDa) for the leaf-movement factor, potassium lespedezate (1), are contained in the plasma membrane of the plant motor cell by using novel synthetic photoaffinity probes. These proteins are localized on the motor cell in the plant body, and would be potential receptors for the leaf-movement factor to control the leaf-movement. Our study is a rare successful result of the detection of membrane receptors by using a synthetic photoaffinity probe designed on a biologically active natural product. And these results also advance a guideline for probe design towards successful photoaffinity labeling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.022
• 作为产物：
  描述：

  t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate 在 吡啶 、 sodium azide 、 15-冠醚-5 、 四丁基氟化铵 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.08h， 生成 t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-azido-6'-deoxy-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate
  参考文献：
  名称：

  Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes

  摘要：

  Circadian rhythmic plant leaf-movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We revealed that specific binding proteins (210 and 180 kDa) for the leaf-movement factor, potassium lespedezate (1), are contained in the plasma membrane of the plant motor cell by using novel synthetic photoaffinity probes. These proteins are localized on the motor cell in the plant body, and would be potential receptors for the leaf-movement factor to control the leaf-movement. Our study is a rare successful result of the detection of membrane receptors by using a synthetic photoaffinity probe designed on a biologically active natural product. And these results also advance a guideline for probe design towards successful photoaffinity labeling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.022

文献信息

• Synthesis of Staudinger-type Molecular Probe for Catch-and-release Purification of the Binding Protein for Potassium Isolespedezate, a Leaf-closing Substance of Leguminous Plant
  作者：Tomohiko Fujii、Nobuki Kato、Izumi Iwakura、Yoshiyuki Manabe、Minoru Ueda

  DOI：10.1246/cl.2008.52

  日期：2008.1.5

  We synthesized azide-containing photoaffinity probe 1 based on the structure of potassium isolespedezate. This probe can be used for catch-and-release-mechanism purification of binding protein for 1: photo-crosslinking with 1 gave azide-labeled receptor which can be captured by phosphane-linked gel matrix by the Staudinger ligation. After washing the gel, the caught binding protein can be released by the reductive cleavage of disulfide bond in 1. This process can be used as a convenient method for the purification of binding protein for bioactive natural product.

  我们根据异双哌酸钾的结构合成了含叠氮化物的光亲和探针1。该探针可用于结合蛋白的捕获和释放机制纯化，与 1 个给定叠氮化物标记的受体进行 1: 光交联，该受体可通过 Staudinger 连接被磷烷连接的凝胶基质捕获。洗涤凝胶后，捕获的结合蛋白可通过1中二硫键的还原断裂而释放。该过程可作为纯化具有生物活性的天然产物的结合蛋白的便捷方法。
• Nanometer-scale direct observation of the receptor for the leaf-movement factor in plant cell by a novel TEM probe
  作者：Yoshiyuki Manabe、Takanori Sugimoto、Tomoyuki Kawasaki、Minoru Ueda

  DOI：10.1016/j.tetlet.2006.12.128

  日期：2007.2

  Electron microscopy is a useful method for observing localization of some proteins in a cell. In this Letter, we report a nanometer-scale direct observation of the receptor for a bioactive substance of small molecular weight by using TEM (transmission electron microscopy). We developed a novel TEM probe compound (1) that is a modified leaf-movement factor with benzophenone as a photoaffinity group and FITC as an antigen that is recognized by a nano-gold bound anti-FITC antibody. By using probe 1, we revealed that the receptor for the leaf-movement factor of Cassia mimosoides is localized in the plasma membrane of the plant motor cell. (c) 2007 Elsevier Ltd. All rights reserved.
• Detection of potential membrane receptor proteins concerning circadian rhythmic leaf movement of legumes using novel photoaffinity probe compounds
  作者：Takanori Sugimoto、Tomohiko Fujii、Yuusuke Idutu、Shosuke Yamamura、Minoru Ueda

  DOI：10.1016/j.tetlet.2003.10.150

  日期：2004.1

  Circadian rhythmic plant leaf movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We report that specific binding protein (210 and 108 kDa) for a leaf movement factor, potassium lespedezate, is contained in the plasma membrane of the plant motor cell. These proteins Would be potential receptors for leaf-movement factor to control the leaf movement. (C) 2003 Elsevier Ltd. All rights reserved.
• Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes
  作者：Tomohiko Fujii、Yoshiyuki Manabe、Takanori Sugimoto、Minoru Ueda

  DOI：10.1016/j.tet.2005.06.022

  日期：2005.8

  Circadian rhythmic plant leaf-movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We revealed that specific binding proteins (210 and 180 kDa) for the leaf-movement factor, potassium lespedezate (1), are contained in the plasma membrane of the plant motor cell by using novel synthetic photoaffinity probes. These proteins are localized on the motor cell in the plant body, and would be potential receptors for the leaf-movement factor to control the leaf-movement. Our study is a rare successful result of the detection of membrane receptors by using a synthetic photoaffinity probe designed on a biologically active natural product. And these results also advance a guideline for probe design towards successful photoaffinity labeling. (c) 2005 Elsevier Ltd. All rights reserved.