(2Z,4E)-5-(1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoicacid | 65133-92-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2Z,4E)-5-(1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoicacid
• 英文别名: (±)-7′-nor-abscisic acid；ABA；(2Z,4E)-5-(1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid
• CAS: 65133-92-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: YAFCFUFXKNGXPE-VFAAGJRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-5-(1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoicacid 在 Chiralcel OD HPLC column 作用下， 以 正己烷 、 溶剂黄146 、 异丙醇 为溶剂， 以2.3 mg的产率得到(-)-(2Z,4E)-5-(1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoicacid
  参考文献：
  名称：

  The selectivity of 6-nor-ABA and 7′-nor-ABA for abscisic acid receptor subtypes

  摘要：

  Abscisic acid (ABA), a plant hormone, is involved in many plant development processes and environmental stress responses that are regulated by a Pyrabactin Resistant 1 (PYR)/Pyrabactin Resistant-Like (PYL)/Regulatory Component of ABA Receptor (RCAR) receptor protein-mediated signal transduction pathway. In Arabidopsis thaliana, PYL proteins constitute a 14-member family comprising two distinct subclasses: dimeric receptors (PYR1 and PYL1-PYL3) and monomeric receptors (PYL4-PYL13). The individual contributions of PYL subclasses/subtypes with specific physiological actions are still poorly understood; consequently, the development of PYL subclass/subtype-selective agonists should be useful to reveal the different functions of these receptors. In this study, we focused on the ABA analogs 6-norABA and 70-nor-ABA, which were expected to function as monomeric receptor-selective agonists on the basis of crystal structures of PYL-ABA complexes and sequence alignments of PYL subtypes. In a protein phosphatase 2C (PP2C) assay, the agonist activities of both analogs were lower than those of ABA toward all tested PYL proteins, regardless of subclass/subtype. Nevertheless, we found that 6-nor-ABA acts as a selective agonist at the physiological level: it induced stomatal closure but did not inhibit seed germination and root growth. On the basis of observed inhibitory activity against PP2C among different PYL subtypes, this biological effect of 6-nor-ABA may be attributed to the activity of that agonist on PYL5 and/or PYL6. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.088
• 作为产物：
  描述：

  (Z)-8-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)-9,9-dimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol 在 盐酸 、 sodium cyanide 、 manganese(IV) oxide 、 水 、 溶剂黄146 、 红铝 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 7.5h， 生成 (2Z,4E)-5-(1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoicacid
  参考文献：
  名称：

  The selectivity of 6-nor-ABA and 7′-nor-ABA for abscisic acid receptor subtypes

  摘要：

  Abscisic acid (ABA), a plant hormone, is involved in many plant development processes and environmental stress responses that are regulated by a Pyrabactin Resistant 1 (PYR)/Pyrabactin Resistant-Like (PYL)/Regulatory Component of ABA Receptor (RCAR) receptor protein-mediated signal transduction pathway. In Arabidopsis thaliana, PYL proteins constitute a 14-member family comprising two distinct subclasses: dimeric receptors (PYR1 and PYL1-PYL3) and monomeric receptors (PYL4-PYL13). The individual contributions of PYL subclasses/subtypes with specific physiological actions are still poorly understood; consequently, the development of PYL subclass/subtype-selective agonists should be useful to reveal the different functions of these receptors. In this study, we focused on the ABA analogs 6-norABA and 70-nor-ABA, which were expected to function as monomeric receptor-selective agonists on the basis of crystal structures of PYL-ABA complexes and sequence alignments of PYL subtypes. In a protein phosphatase 2C (PP2C) assay, the agonist activities of both analogs were lower than those of ABA toward all tested PYL proteins, regardless of subclass/subtype. Nevertheless, we found that 6-nor-ABA acts as a selective agonist at the physiological level: it induced stomatal closure but did not inhibit seed germination and root growth. On the basis of observed inhibitory activity against PP2C among different PYL subtypes, this biological effect of 6-nor-ABA may be attributed to the activity of that agonist on PYL5 and/or PYL6. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.088