1-(1,3-dihydroxybut-1-yl)-β-carboline

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(1,3-dihydroxybut-1-yl)-β-carboline
• 英文别名: 1-(9H-pyrido[3,4-b]indol-1-yl)butane-1,3-diol
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: HGJNNAVMBMMGQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.14
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  D-核糖 、 L-色氨酸 在 盐酸 作用下， 反应 744.0h， 生成 1-(1,3-dihydroxybut-1-yl)-β-carboline
  参考文献：
  名称：

  Reaction of Tryptophan with Carbohydrates:  Mechanistic Studies on the Formation of Carbohydrate-Derived β-Carbolines

  摘要：

  Numerous carbohydrate-derived beta -carbolines have been identified for the first time in model reactions of tryptophan with glucose and ribose, as well as in food samples. Extending these structural studies, we performed detailed investigations to elucidate the corresponding intermediates and formation pathway of these alkaloids. Degradation experiments with purified tryptophan glycoconjugates established that only glyco-tetrahydro-beta -carboline-3-carboxylic acids, and not the N-glycosides nor the C-glycoconjugates represented the direct precursors of carbohydrate-derived beta -carbolines. In addition, the significance of the oxidative decarboxylation reaction as the initial step for formation of 1-substituted beta -carbolines was proven. Finally, the stereochemistry of the carbohydrate-derived side chain was studied by means of CD spectroscopy and HPLC-CD experiments. These detailed stereochemical analyses yielded experimental evidence for the racemization steps required for formation of the carbohydrate-derived harman alkaloids and confirmed the proposed reaction pathway.

  DOI：

  10.1021/jf010379o

文献信息

• Reaction of Tryptophan with Carbohydrates:  Mechanistic Studies on the Formation of Carbohydrate-Derived <i>β</i>-Carbolines
  作者：Stefanie Diem、Markus Herderich

  DOI：10.1021/jf010379o

  日期：2001.11.1

  Numerous carbohydrate-derived beta -carbolines have been identified for the first time in model reactions of tryptophan with glucose and ribose, as well as in food samples. Extending these structural studies, we performed detailed investigations to elucidate the corresponding intermediates and formation pathway of these alkaloids. Degradation experiments with purified tryptophan glycoconjugates established that only glyco-tetrahydro-beta -carboline-3-carboxylic acids, and not the N-glycosides nor the C-glycoconjugates represented the direct precursors of carbohydrate-derived beta -carbolines. In addition, the significance of the oxidative decarboxylation reaction as the initial step for formation of 1-substituted beta -carbolines was proven. Finally, the stereochemistry of the carbohydrate-derived side chain was studied by means of CD spectroscopy and HPLC-CD experiments. These detailed stereochemical analyses yielded experimental evidence for the racemization steps required for formation of the carbohydrate-derived harman alkaloids and confirmed the proposed reaction pathway.