methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate | 295797-74-9

• 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'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
• 英文别名: methyl (Z)-2-[(2S,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 295797-74-9
• 化学式: C₁₆H₁₉N₃O₈
• 分子量: 381.342
• InChiKey: MLLBECJJAJSUNU-PGMBCTCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate 在 Lindlar's catalyst 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl (Z)-2-[6'-(N-benzyloxycarbonylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenylacrylate
  参考文献：
  名称：

  Synthetic Probe Compounds for Bioorganic Studies of Nyctinasty, Based on the Leaf-opening Substance of Lespedeza cuneata G. Don

  摘要：

  In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezate (3) and iodo-one (4), designed on the basis of 1 and 2 were prepared. Especially, compound 3 was bioactive at 5x10(-5) M, one-fiftieth as strong as the natural leaf-opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00421-x
• 作为产物：
  描述：

  (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester 在 吡啶 、 sodium azide 、 15-冠醚-5 、 四丁基氟化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
  参考文献：
  名称：

  Syntheses of fluorescence-labeled artificial leaf-opening substances, fluorescent probe compounds useful for bioorganic studies of nyctinasty

  摘要：

  In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezates (3, 10, 13), designed on the basis of 1 and 2, were prepared. In particular, compound 3 was bioactive at 5 X 10(-5) M, one-fiftieth as strong as the natural leaf-opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00394-4

文献信息

• Visualization of the Precise Structure Recognition of Leaf-opening Substance by Using Biologically Inactive Probe Compounds: Fluorescence Studies of Nyctinasty in Legumes 2
  作者：Takanori Sugimoto、Shosuke Yamamura、Minoru Ueda

  DOI：10.1246/cl.2002.1118

  日期：2002.11

  Intimate correlation between bioactivity and binding activity was shown using biologically active and inactive fluorescence-labeled probe compounds for nyctinasty. This results suggested the existence of a receptor which recognizes the aglycon of a leaf-opening substance on the motor cell.

  使用生物活性和非生物活性荧光标记探针化合物对夜光性进行了研究，结果表明生物活性和结合活性之间存在密切关联。研究结果表明，存在一种受体，能够识别运动细胞上叶片张开物质的糖苷。
• Syntheses of fluorescence-labeled artificial leaf-opening substances, fluorescent probe compounds useful for bioorganic studies of nyctinasty
  作者：Minoru Ueda、Yoshiyuki Sawai、Shosuke Yamamura

  DOI：10.1016/s0040-4039(00)00394-4

  日期：2000.4

  In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezates (3, 10, 13), designed on the basis of 1 and 2, were prepared. In particular, compound 3 was bioactive at 5 X 10(-5) M, one-fiftieth as strong as the natural leaf-opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.
• Synthetic Probe Compounds for Bioorganic Studies of Nyctinasty, Based on the Leaf-opening Substance of Lespedeza cuneata G. Don
  作者：Minoru Ueda、Yoshiyuki Sawai、Yoko Wada、Shosuke Yamamura

  DOI：10.1016/s0040-4020(00)00421-x

  日期：2000.7

  In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezate (3) and iodo-one (4), designed on the basis of 1 and 2 were prepared. Especially, compound 3 was bioactive at 5x10(-5) M, one-fiftieth as strong as the natural leaf-opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd. All rights reserved.