t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate | 544703-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate
• 英文别名: tert-butyl 3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxypropanoate
• CAS: 544703-52-8
• 化学式: C₃₉H₅₁NO₁₃Si
• 分子量: 769.918
• InChiKey: XMWJLLDFSPCHKC-QTKXPZBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate 在 Lindlar's catalyst 吡啶 、 sodium azide 、 15-冠醚-5 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 1-羟基苯并三唑 、 一水合肼 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 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 、 乙腈 为溶剂， 反应 136.08h， 生成 t-butyl (Z)-2-(2'-deoxy-2'-[4-benzoylphenyl]methylamino-6'-[N-(N-(N-(biotinyl)glycyl)glycyl)glycyl]-amino-6'-deoxy-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-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：

  D-(+)-galactosamine hydrochloride 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 氢溴酸 、 氢气 、 silver trifluoromethanesulfonate 、 乙酸酐 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate
  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 a novel bioactive photoaffinity probe based on a leaf-movement factor with potential high binding affinity to its receptor molecule
  作者：Tomohiko Fujii、Takanori Sugimoto、Shosuke Yamamura、Minoru Ueda

  DOI：10.1016/s0040-4039(03)00287-9

  日期：2003.3

  located in the pulvini of the plant. Some receptors of the leaf-movement factor should be involved in this biological event. We developed a novel photoaffinity probe (1) for the detection of receptor molecules. Probe compound 1 bears a photolabeling group on the 2′-position of the glycon moiety, which is near the potential binding site of the molecule with its receptor. This molecular design would be effective

  叶片运动因子与植物小叶植物中运动细胞的结合诱导了芥子叶运动。叶片运动因子的某些受体应参与此生物学事件。我们开发了一种新型的光亲和探针（1）用于检测受体分子。探针化合物1在糖苷部分的2'-位置带有一个光标记基团，该基团靠近该分子与其受体的潜在结合位点。这种分子设计对于提高光标记产率是有效的。