(S)-2-trans-abscisate

• 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: (S)-2-trans-abscisate
• 英文别名: (2E,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate
• 化学式: C15H19O4-
• 分子量: 263.31
• InChiKey: JLIDBLDQVAYHNE-IBPUIESWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-trans-abscisate 、 UDP-glucose 生成 (S)-2-trans-abscisic acid beta-D-glucopyranosyl ester 、 UDP
  参考文献：
  名称：

  Cloning and Characterization of the Abscisic Acid-Specific Glucosyltransferase Gene from Adzuki Bean Seedlings

  摘要：

  已经从许多植物物种中鉴定出了葡萄糖化的脱落酸（ABA）形式，并且已知它们是ABA降解的形式，尽管它们的（生理）作用尚未阐明。ABA葡萄糖转移酶（-GTase）被认为在ABA的葡萄糖化中发挥关键作用。我们从小豆（Vigna angularis）幼苗中获得的UDP-GTase同源物中分离出了一个ABA诱导的GTase基因。推导的氨基酸序列（存取号AB065190）与已知的UDP-GTase同源物相比，显示出30％至44％的同一性。带有谷胱甘肽S-转移酶标签的重组蛋白在大肠杆菌中表达，并以ABA特异性方式显示出酶活性。在柠檬酸和Tris-HCl缓冲液中，在pH 5.0至9.0的宽范围内检测到酶活性，最佳范围在pH 6.0至7.3之间。通过气相色谱/质谱法确定了来自拉丁式ABA和UDP-d-葡萄糖的产物为ABA-GE。重组GTase（rAOG）比（+）-S-ABA和（-）-R-ABA更好地转化2-反式（+）-ABA。虽然GTase轻微地将反-肉桂酸转化为其结合物，但（-）-PA则没有。mRNA水平通过ABA应用或水分胁迫和损伤而增加。我们认为该基因编码ABA特异性GTase，并且其表达受环境胁迫调节。

  DOI：

  10.1104/pp.001784

文献信息

• Cloning and Characterization of the Abscisic Acid-Specific Glucosyltransferase Gene from Adzuki Bean Seedlings
  作者：Zheng-Jun Xu、Masatoshi Nakajima、Yoshihito Suzuki、Isomaro Yamaguchi

  DOI：10.1104/pp.001784

  日期：2002.7.1

  The glycosylated forms of abscisic acid (ABA) have been identified from many plant species and are known to be the forms of ABA-catabolism, although their (physiological) roles have not yet been elucidated. ABA-glucosyltransferase (-GTase) is thought to play a key role in the glycosylation of ABA. We isolated an ABA-inducible GTase gene from UDP-GTase homologs obtained from adzuki bean (Vigna angularis) seedlings. The deduced amino acid sequence (accession no. AB065190) showed 30% to 44% identity with the known UDP-GTase homologs. The recombinant protein with a glutathioneS-transferase-tag was expressed in Escherichia coli and showed enzymatic activity in an ABA-specific manner. The enzymatic activity was detected over a wide pH range from 5.0 to 9.0, the optimum range being between pH 6.0 and 7.3, in a citrate and Tris-HCl buffer. The product from racemic ABA and UDP-d-glucose was identified to be ABA-GE by gas chromatography/mass spectrometry. The recombinant GTase (rAOG) converted 2-trans-(+)-ABA better than (+)-S-ABA and (−)-R-ABA. Although trans-cinnamic acid was slightly converted to its conjugate by the GTase, (−)-PA was not at all. The mRNA level was increased by ABA application or by water stress and wounding. We suggest that the gene encodes an ABA-specific GTase and that its expression is regulated by environmental stress.

  已经从许多植物物种中鉴定出了葡萄糖化的脱落酸（ABA）形式，并且已知它们是ABA降解的形式，尽管它们的（生理）作用尚未阐明。ABA葡萄糖转移酶（-GTase）被认为在ABA的葡萄糖化中发挥关键作用。我们从小豆（Vigna angularis）幼苗中获得的UDP-GTase同源物中分离出了一个ABA诱导的GTase基因。推导的氨基酸序列（存取号AB065190）与已知的UDP-GTase同源物相比，显示出30％至44％的同一性。带有谷胱甘肽S-转移酶标签的重组蛋白在大肠杆菌中表达，并以ABA特异性方式显示出酶活性。在柠檬酸和Tris-HCl缓冲液中，在pH 5.0至9.0的宽范围内检测到酶活性，最佳范围在pH 6.0至7.3之间。通过气相色谱/质谱法确定了来自拉丁式ABA和UDP-d-葡萄糖的产物为ABA-GE。重组GTase（rAOG）比（+）-S-ABA和（-）-R-ABA更好地转化2-反式（+）-ABA。虽然GTase轻微地将反-肉桂酸转化为其结合物，但（-）-PA则没有。mRNA水平通过ABA应用或水分胁迫和损伤而增加。我们认为该基因编码ABA特异性GTase，并且其表达受环境胁迫调节。