methyl (Z)-2-[6'-(6-((7-amino-4-methylcoumarin-3-acetyl)amino)-hexanamide)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate | 397884-06-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (Z)-2-[6'-(6-((7-amino-4-methylcoumarin-3-acetyl)amino)-hexanamide)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate
• 英文别名: methyl (Z)-2-[(2S,3R,4S,5R,6R)-6-[[6-[[2-(7-amino-4-methyl-2-oxochromen-3-yl)acetyl]amino]hexanoylamino]methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 397884-06-9
• 化学式: C₃₄H₄₁N₃O₁₂
• 分子量: 683.712
• InChiKey: CNPRJUQMNYFTPF-DWEXAKNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  236
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-[6'-(6-((7-amino-4-methylcoumarin-3-acetyl)amino)-hexanamide)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (Z)-2-[6'-(6-((7-amino-4-methylcoumarin-3-acetyl)amino)hexanamide)-β-D-galactopyranosyloxy]-3-p-hydroxyphenylacrylate, potassium salt
  参考文献：
  名称：

  Direct observation of the target cell for leaf-movement factor using novel fluorescence-labeled probe compounds: fluorescence studies of nyctinasty in legumes. Part 1

  摘要：

  We synthesized fluorescence-labeled probe compounds hearing AMCA (1). NBD (2). and dansyl (3) groups as the fluorescent functionality, In these probe compounds. NBD-type probe. 2. showed leaf-opening activity at 5x10(-6) M. The bioactivity of 2 is one-fifth as strong as that of the natural product, potassium isolespedezate (6). We carried out the binding experiment using 1 in a plant body. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00589-5
• 作为产物：
  描述：

  methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate 在 Lindlar's catalyst TEA 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 methyl (Z)-2-[6'-(6-((7-amino-4-methylcoumarin-3-acetyl)amino)-hexanamide)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate
  参考文献：
  名称：

  Fluorescence study on the nyctinasty of Cassia mimosoides L. using novel fluorescence-labeled probe compounds

  摘要：

  We synthesized fluorescence-labeled probe compounds bearing 6-((7-amino-4-methylcoumarin-3-acetyl)amino)-hexanoyl (AMCA, 1), 6-N-(7-nitrobenz-2-oxa-1, 3-diazol-4-yl)-aminohexanoyl (NBD, 2), and 6-(4-((5-dimethylaminonaphthalene-1-sulfonyl)amino))-hexanoyl (dansyl, 3) groups as the fluorescent functionality. In these probe compounds, NBD-type probe, 2, showed leaf-opening activity at 5 X 10(-6) M. The bioactivity of 2 is one-fifth as strong as that of the natural product, potassium isolespedezate (6). We carried out the binding experiment using 1 in a plant body. Then, it was suggested that fluorescence-labeled probe compound directly bound to a motor cell in pulvina of Cassia mimosoides. And this binding was specific to C. mimosoides. Probe compounds cannot bind plant sections of other nyctinastic plants. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00999-1

文献信息

• Fluorescence study on the nyctinasty of Cassia mimosoides L. using novel fluorescence-labeled probe compounds
  作者：Takanori Sugimoto、Yoko Wada、Shosuke Yamamura、Minoru Ueda

  DOI：10.1016/s0040-4020(01)00999-1

  日期：2001.12

  We synthesized fluorescence-labeled probe compounds bearing 6-((7-amino-4-methylcoumarin-3-acetyl)amino)-hexanoyl (AMCA, 1), 6-N-(7-nitrobenz-2-oxa-1, 3-diazol-4-yl)-aminohexanoyl (NBD, 2), and 6-(4-((5-dimethylaminonaphthalene-1-sulfonyl)amino))-hexanoyl (dansyl, 3) groups as the fluorescent functionality. In these probe compounds, NBD-type probe, 2, showed leaf-opening activity at 5 X 10(-6) M. The bioactivity of 2 is one-fifth as strong as that of the natural product, potassium isolespedezate (6). We carried out the binding experiment using 1 in a plant body. Then, it was suggested that fluorescence-labeled probe compound directly bound to a motor cell in pulvina of Cassia mimosoides. And this binding was specific to C. mimosoides. Probe compounds cannot bind plant sections of other nyctinastic plants. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Direct observation of the target cell for leaf-movement factor using novel fluorescence-labeled probe compounds: fluorescence studies of nyctinasty in legumes. Part 1
  作者：Minoru Ueda、Yoko Wada、Shosuke Yamamura

  DOI：10.1016/s0040-4039(01)00589-5

  日期：2001.6

  We synthesized fluorescence-labeled probe compounds hearing AMCA (1). NBD (2). and dansyl (3) groups as the fluorescent functionality, In these probe compounds. NBD-type probe. 2. showed leaf-opening activity at 5x10(-6) M. The bioactivity of 2 is one-fifth as strong as that of the natural product, potassium isolespedezate (6). We carried out the binding experiment using 1 in a plant body. (C) 2001 Elsevier Science Ltd. All rights reserved.