N-acetyl-DL-[1'',1'',1''-(2)H3]-1'-methoxytryptophan | 1190220-86-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-DL-[1'',1'',1''-(2)H3]-1'-methoxytryptophan
• CAS: 1190220-86-0
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 279.268
• InChiKey: MPIYYEZGTOTRPW-BMSJAHLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-acetyl-DL-[1'',1'',1''-(2)H3]-1'-methoxytryptophan 在 L-aminoacylase 、 cobalt(II) chloride hexahydrate 作用下， 反应 24.0h， 以30%的产率得到L-[1'',1'',1''-(2)H3]-1'-methoxytryptophan
  参考文献：
  名称：

  The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: De novo incorporation of deuterated tryptophans and quasi-natural compounds

  摘要：

  Although several biosynthetic intermediates in pathways to cruciferous phytoalexins and phytoanticipins are common, questions regarding the introduction of substituents at N-1 of the indole moiety remain unanswered. Toward this end, we investigated the potential incorporations of several perdeuterated D- and L-1'-methoxytryptophans, D- and L-tryptophans and other indol-3-yl derivatives into pertinent phytoalexins and phytoanticipins (indolyl glucosinolates) produced in rutabaga (Brassica napus L. ssp. rapifera) roots. In addition, we probed the potential transformations of quasi-natural compounds, these being analogues of biosynthetic intermediates that might lead to "quasi-natural" products (products similar to natural products but not produced under natural conditions). No detectable incorporations of deuterium labeled 1'-methoxytryptophans into phytoalexins or glucobrassicin were detected. L-tryptophan was incorporated in a higher percentage than D-tryptophan into both phytoalexins and phytoanticipins. However, in the case of the phytoalexin rapalexin A, both D- and L-tryptophan were incorporated to the same extent. Furthermore, the transformations of both 1'-methylindolyl-3'-acetaldoxime and 1'-methylindolyl-3'-acetothiohydroxamic acid (quasi-natural products) into 1'-methylglucobrassicin but not into phytoalexins suggested that post-aldoxime enzymes in the biosynthetic pathway of indolyl glucosinolates are not substrate-specific. Hence, it would appear that the 1-methoxy substituent of the indole moiety is introduced downstream from tryptophan and that the post-aldoxime enzymes of the glucosinolate pathway are different from the enzymes of the phytoalexin pathway. A higher substrate specificity of some enzymes of the phytoalexin pathway might explain the relatively lower structural diversity among phytoalexins than among glucosinolates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.05.015
• 作为产物：
  描述：

  DL-丝氨酸 、 乙酸酐 、 溶剂黄146 、 [1',1',1'-(2)H3]-1-methoxyindole 反应 2.0h， 以75%的产率得到N-acetyl-DL-[1'',1'',1''-(2)H3]-1'-methoxytryptophan
  参考文献：
  名称：

  The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: De novo incorporation of deuterated tryptophans and quasi-natural compounds

  摘要：

  Although several biosynthetic intermediates in pathways to cruciferous phytoalexins and phytoanticipins are common, questions regarding the introduction of substituents at N-1 of the indole moiety remain unanswered. Toward this end, we investigated the potential incorporations of several perdeuterated D- and L-1'-methoxytryptophans, D- and L-tryptophans and other indol-3-yl derivatives into pertinent phytoalexins and phytoanticipins (indolyl glucosinolates) produced in rutabaga (Brassica napus L. ssp. rapifera) roots. In addition, we probed the potential transformations of quasi-natural compounds, these being analogues of biosynthetic intermediates that might lead to "quasi-natural" products (products similar to natural products but not produced under natural conditions). No detectable incorporations of deuterium labeled 1'-methoxytryptophans into phytoalexins or glucobrassicin were detected. L-tryptophan was incorporated in a higher percentage than D-tryptophan into both phytoalexins and phytoanticipins. However, in the case of the phytoalexin rapalexin A, both D- and L-tryptophan were incorporated to the same extent. Furthermore, the transformations of both 1'-methylindolyl-3'-acetaldoxime and 1'-methylindolyl-3'-acetothiohydroxamic acid (quasi-natural products) into 1'-methylglucobrassicin but not into phytoalexins suggested that post-aldoxime enzymes in the biosynthetic pathway of indolyl glucosinolates are not substrate-specific. Hence, it would appear that the 1-methoxy substituent of the indole moiety is introduced downstream from tryptophan and that the post-aldoxime enzymes of the glucosinolate pathway are different from the enzymes of the phytoalexin pathway. A higher substrate specificity of some enzymes of the phytoalexin pathway might explain the relatively lower structural diversity among phytoalexins than among glucosinolates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.05.015