(Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester | 287934-39-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester
• CAS: 287934-39-8
• 化学式: C₁₆H₂₁NO₈
• 分子量: 355.345
• InChiKey: OWMVHBNIARIMRP-PGMBCTCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  151.7
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (Z)-2-[6'-(glycylglycylglycyl-5-thioureidylfluorescein)-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
• 作为产物：
  描述：

  methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate 在 Lindlar's catalyst 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester
  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

文献信息

• Syntheses of novel photoaffinity probes for bioorganic studies on nyctinasty of leguminous plants
  作者：Takanori Sugimoto、Tomohiko Fujii、Yasumaru Hatanaka、Shosuke Yamamura、Minoru Ueda

  DOI：10.1016/s0040-4039(02)01460-0

  日期：2002.9

  Novel and non-radioactive photoaffinity probes (1 and 2) for the bioorganic Study of nyctinasty are designed and synthesized based on potassium isolespedezate (3), which induce leaf-opening against the leaf of Cassia mimosoides L. These probes bear a trifluoromethyldiazirine or diazophenyl group for photoaffinity and a biotin Subunit for affinity chromatography and chemiluminescent detection. Probes (1 and 2) showed leaf-opening activity at 5x10(-5) mol/L with leaves of C. mimosoides; thus, they would be an important tool for the identification of a receptor protein for 3. (C) 2002 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.