{(1R,2R)-2-[(Z)-5-((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-pent-2-enyl]-3-oxo-cyclopentyl}-acetic acid | 885466-37-5

• 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: {(1R,2R)-2-[(Z)-5-((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-pent-2-enyl]-3-oxo-cyclopentyl}-acetic acid
• 英文别名: 2-[(1R,2R)-2-[(Z)-5-[(2R,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxypent-2-enyl]-3-oxocyclopentyl]acetic acid
• CAS: 885466-37-5
• 化学式: C₁₈H₂₉NO₈
• 分子量: 387.43
• InChiKey: JCGHPIZHVLBPDE-BHBLQNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  {(1R,2R)-2-[(Z)-5-((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-pent-2-enyl]-3-oxo-cyclopentyl}-acetic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 生成
  参考文献：
  名称：

  Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

  摘要：

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.092
• 作为产物：
  描述：

  methyl 12-hydroxyjasmonate 在 氢氧化钾 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 {(1R,2R)-2-[(Z)-5-((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-pent-2-enyl]-3-oxo-cyclopentyl}-acetic acid
  参考文献：
  名称：

  Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

  摘要：

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.092

文献信息

• Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds
  作者：Yoko Nakamura、Ryoji Miyatake、Akira Matsubara、Hiromasa Kiyota、Minoru Ueda

  DOI：10.1016/j.tet.2006.06.092

  日期：2006.9

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.