(1H-indol-3-yl)-N-methylmethanamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1H-indol-3-yl)-N-methylmethanamine
• 英文别名: 1H-indol-3-ylmethyl(methyl)azanium
• 化学式: C10H13N2+
• 分子量: 161.22
• InChiKey: BIFJNBXQXNWYOL-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.4
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1H-indol-3-yl)-N-methylmethanamine 、 S-腺苷蛋氨酸 生成 1-(1H-indol-1-ium-3-yl)-N,N-dimethylmethanamine 、 氢(+1)阳离子 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  Induction of a Specific N-Methyltransferase Enzyme by Long-Term Heat Stress during Barley Leaf Growth

  摘要：

  之前的研究表明，靛基生物碱类化合物草碱在大麦上部叶片（如第五片）中积累，以应对高温生长。草碱的生物合成从色氨酸开始，生成3-氨基甲基吲哚（AMI）；AMI依次进行N-甲基化，生成N-甲基-3-氨基甲基吲哚（MAMI）和草碱。为了确定高温胁迫是否增加草碱途径酶的活性，在体内和体外实验中，以AMI和MAMI为底物，对在不同温度下生长的植物的叶片组织中的N-甲基转移酶（NMT）活性进行了检测。与低温（15°C/10°C）相比，高温（35°C/30°C）下生长的第五片叶片中的NMT活性增加了8-20倍。需要数天的高温才能完全诱导NMT活性。在高温之前，在低温条件下完全展开的叶片中不会发生NMT活性的诱导。为了在蛋白质水平上研究NMT的诱导，将NMT活性纯化为均相，并用于制备多克隆抗体。在整个酶纯化过程中，AMI和MAMI的相对NMT活性保持恒定，与单个NMT酶一致。免疫印迹分析表明，NMT多肽的大量增加与热胁迫诱导的NMT活性相吻合。我们的研究结果表明，高温调节基因

  DOI：

  10.1104/pp.79.2.451
• 作为产物：
  描述：

  1H-indol-3-ylmethylazanium 、 S-腺苷蛋氨酸 生成 (1H-indol-3-yl)-N-methylmethanamine 、 氢(+1)阳离子 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  Induction of a Specific N-Methyltransferase Enzyme by Long-Term Heat Stress during Barley Leaf Growth

  摘要：

  之前的研究表明，靛基生物碱类化合物草碱在大麦上部叶片（如第五片）中积累，以应对高温生长。草碱的生物合成从色氨酸开始，生成3-氨基甲基吲哚（AMI）；AMI依次进行N-甲基化，生成N-甲基-3-氨基甲基吲哚（MAMI）和草碱。为了确定高温胁迫是否增加草碱途径酶的活性，在体内和体外实验中，以AMI和MAMI为底物，对在不同温度下生长的植物的叶片组织中的N-甲基转移酶（NMT）活性进行了检测。与低温（15°C/10°C）相比，高温（35°C/30°C）下生长的第五片叶片中的NMT活性增加了8-20倍。需要数天的高温才能完全诱导NMT活性。在高温之前，在低温条件下完全展开的叶片中不会发生NMT活性的诱导。为了在蛋白质水平上研究NMT的诱导，将NMT活性纯化为均相，并用于制备多克隆抗体。在整个酶纯化过程中，AMI和MAMI的相对NMT活性保持恒定，与单个NMT酶一致。免疫印迹分析表明，NMT多肽的大量增加与热胁迫诱导的NMT活性相吻合。我们的研究结果表明，高温调节基因

  DOI：

  10.1104/pp.79.2.451

文献信息

• Induction of a Specific <i>N</i>-Methyltransferase Enzyme by Long-Term Heat Stress during Barley Leaf Growth
  作者：Timothy J. Leland、Andrew D. Hanson

  DOI：10.1104/pp.79.2.451

  日期：1985.10.1

  Previous work showed that the indole alkaloid gramine accumulates in the upper leaves (e.g. the fifth) of barley as a response to high growth temperatures. The biosynthesis of gramine proceeds from tryptophan to 3-aminomethylindole (AMI); sequential N-methylations of AMI then yield N-methyl-3-aminomethylindole (MAMI) and gramine.To determine whether high-temperature stress increases the activity of gramine pathway enzymes, leaf tissue from plants grown at various temperatures was assayed for N-methyltransferase (NMT) activity using AMI and MAMI as substrates in both in vivo and in vitro assays. NMT activity in expanding fifth leaves was increased 8- to 20-fold by growth at high temperatures (35°C day/30°C night) compared to cool temperatures (15°C/10°C). Several days of high temperature were required for full induction of NMT activity. No induction of NMT activity occurred in leaves which had completed expansion in cool conditions before exposure to high temperature.To investigate NMT induction at the protein level, NMT activity was purified to homogeneity and used to produce polyclonal antibodies. Throughout enzyme purification, relative NMT activities towards AMI and MAMI remained constant, consistent with a single NMT enzyme. Immunoblot analysis showed that a large increase in NMT polypeptide coincided with induction of NMT activity by heat stress. Our results point to a type of high-temperature regulation of gene expression that is quite distinct from heat shock.

  之前的研究表明，靛基生物碱类化合物草碱在大麦上部叶片（如第五片）中积累，以应对高温生长。草碱的生物合成从色氨酸开始，生成3-氨基甲基吲哚（AMI）；AMI依次进行N-甲基化，生成N-甲基-3-氨基甲基吲哚（MAMI）和草碱。为了确定高温胁迫是否增加草碱途径酶的活性，在体内和体外实验中，以AMI和MAMI为底物，对在不同温度下生长的植物的叶片组织中的N-甲基转移酶（NMT）活性进行了检测。与低温（15°C/10°C）相比，高温（35°C/30°C）下生长的第五片叶片中的NMT活性增加了8-20倍。需要数天的高温才能完全诱导NMT活性。在高温之前，在低温条件下完全展开的叶片中不会发生NMT活性的诱导。为了在蛋白质水平上研究NMT的诱导，将NMT活性纯化为均相，并用于制备多克隆抗体。在整个酶纯化过程中，AMI和MAMI的相对NMT活性保持恒定，与单个NMT酶一致。免疫印迹分析表明，NMT多肽的大量增加与热胁迫诱导的NMT活性相吻合。我们的研究结果表明，高温调节基因
• N-Methyltransferase involved in gramine biosynthesis in barley: Cloning and characterization
  作者：Kristina A.E. Larsson、Ingvor Zetterlund、Gabriele Delp、Lisbeth M.V. Jonsson

  DOI：10.1016/j.phytochem.2006.06.036

  日期：2006.9

  The indole alkaloid gramine occurs in leaves of certain barley (Hordeum vulgare L.) cultivars but not in others. A gene sequence in barley that earlier was characterized as a jasmonate-induced O-methyltransferase (MT) (EC 2.1.1.6, GenBank accession U54767) was here found to be absent in some barley cultivars and breeding lines that all lacked gramine. The cDNA was cloned and expressed in Escherichia coli and the recombinant protein purified. The purified recombinant protein methylated two substrates in the pathway to gramine: 3-aminomethylindole (AMI) and N-methyl-3-aminomethylindole (MAMI) at a high rate, with Km-values of 77 mu M and 184 mu M, respectively. In contrast, the protein did not exhibit any detectable methylation with the earlier suggested substrate for O-methylation, caffeic acid. A number of cultivars and breeding lines of barley were analyzed for presence of the U54767 gene sequence and NIT protein and the enzyme activity in vitro with MAMI or caffeic acid as substrates. The results showed a clear relationship between the presence of the MT gene, the NIT protein and N-methyltransferase activity, and confirmed the identification of the gene as coding for an N-methyltransferase (NMT, EC 2.1.1) and being involved in gramine biosynthesis. (c) 2006 Elsevier Ltd. All rights reserved.