(2Z,4E)-5-(2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadiene

• 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-(2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadiene
• 英文别名: (2Z,4E)-α-ionylideneethane；2Z,4E-alpha-Ionylideneethane；(6R)-1,5,5-trimethyl-6-[(1E,3Z)-3-methylpenta-1,3-dienyl]cyclohexene
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: IWKFTSBVCOXJTI-GORXRUJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  farnesyl pyrophosphate 在 乙二胺四乙酸 、 1,4-dithio-D,L-threitol 、 recombinant α-ionylideneethane synthase BcABA3 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 生成 (2Z,4E)-5-(2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadiene
  参考文献：
  名称：

  揭示真菌中植物激素脱落酸的生物合成：由不寻常的倍半萜烯合酶催化的核心支架形成的前所未有的机制

  摘要：

  脱落酸（ABA）是一种众所周知的调节非生物胁迫的植物激素。真菌产生的 ABA 也被认为是真菌病原体的毒力因子。尽管其在真菌中的生物合成途径是由一系列饲养实验提出的，但催化法呢基二磷酸到 α-亚亚乙基乙烷反应的酶仍有待确定。在这项工作中，我们确定了新型倍半萜烯合酶 BcABA3 及其前所未有的三步反应机制，涉及两种中性中间体，β-法呢烯和异法呢烯。数据库搜索表明，BcABA3与典型的倍半萜合酶没有同源性，在100多种细菌中发现了同源酶基因，表明这些酶形成了一个新的倍半萜合酶家族。

  DOI：

  10.1021/jacs.8b08925

文献信息

• The biosynthetic pathway to abscisic acid via ionylideneethane in the fungus Botrytis cinerea
  作者：Masahiro Inomata、Nobuhiro Hirai、Ryuji Yoshida、Hajime Ohigashi

  DOI：10.1016/j.phytochem.2004.08.025

  日期：2004.10

  The biosynthetic pathway to abscisic acid (ABA) from isopentenyl diphosphate in the fungus, Botrytis cinerea, was investigated. Labeling experiments with O-18(2) and (H2O)-O-18 indicated that all oxygen atoms at C1, -1, -1' and -4' of ABA were derived from molecular oxygen, and not from water. This finding was inconsistent not only with the known carotenoid pathway via oxidative cleavage of carotenoids, but also with the classical direct pathway via cyclization of farnesyl diphosphate. The fungus produced new C-15-compounds, 2E,4E-alpha-ionylideneethane and 2Z,4E-alpha-ionylideneethane, along with 2E,4E,6E-allofarnesene and 2Z,4E,6E-allofarnesene, but did not apparently produce carotenoids except for a trace of phytoene. The C-15-compounds labeled with C-13 were converted to ABA by the fungus, and the incorporation ratio of 2Z,4E-alpha-ionylideneethane was higher than that of 2E,4E-alpha-ionylideneethane. From these results, it was concluded that farnesyl diphosphate was reduced at C-1, desaturated at C-4, and isomerized at C-2 to form 2Z,4E,6E-allofarnesene before being cyclized to 2Z,4E-alpha-ionylideneethane; the ionylideneethane was then oxidized to ABA with molecular oxygen. This direct pathway via ionylideneethane means that the biosynthetic pathway to fungal ABA, not only before but also after isopentenyl diphosphate, differs from that to ABA in plants, since plant ABA is biosynthesized using the non-mevalonate and carotenoid pathways. (C) 2004 Elsevier Ltd. All rights reserved.
• Unveiling Biosynthesis of the Phytohormone Abscisic Acid in Fungi: Unprecedented Mechanism of Core Scaffold Formation Catalyzed by an Unusual Sesquiterpene Synthase
  作者：Junya Takino、Takuto Kozaki、Yoshiro Sato、Chengwei Liu、Taro Ozaki、Atsushi Minami、Hideaki Oikawa

  DOI：10.1021/jacs.8b08925

  日期：2018.10.3

  novel type of sesquiterpene synthase BcABA3 and its unprecedented three-step reaction mechanism involving two neutral intermediates, β-farnesene and allofarnesene. Database searches showed that BcABA3 has no homology with typical sesquiterpene synthases and that the homologous enzyme genes are found in more than 100 bacteria, suggesting that these enzymes form a new family of sesquiterpene synthases.

  脱落酸（ABA）是一种众所周知的调节非生物胁迫的植物激素。真菌产生的 ABA 也被认为是真菌病原体的毒力因子。尽管其在真菌中的生物合成途径是由一系列饲养实验提出的，但催化法呢基二磷酸到 α-亚亚乙基乙烷反应的酶仍有待确定。在这项工作中，我们确定了新型倍半萜烯合酶 BcABA3 及其前所未有的三步反应机制，涉及两种中性中间体，β-法呢烯和异法呢烯。数据库搜索表明，BcABA3与典型的倍半萜合酶没有同源性，在100多种细菌中发现了同源酶基因，表明这些酶形成了一个新的倍半萜合酶家族。