trans-1-(2'-carboxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

• 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: trans-1-(2'-carboxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: (1R,3S)-1-(2-carboxyethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: PPKGNUKJFFAWHY-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  琥珀半醛 、 L-色氨酸 在 硫酸 作用下， 反应 48.0h， 生成 cis-1-(2'-carboxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 、 trans-1-(2'-carboxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  HPLC−MS/MS Profiling of Tryptophan-Derived Alkaloids in Food:  Identification of Tetrahydro-β-carbolinedicarboxylic Acids

  摘要：

  A method for selective detection of 1,2,3,4-tetrahydro-beta-carbolinecarboxylic acids (THCCs) was developed based on electrospray ionization-tandem mass spectrometry coupled to liquid chromatography (HPLC-ESI-MS/MS). Low-energy collision-induced dissociation (CID) led to characteristic fragment ions due to neutral loss of 73 amu. Subsequently, constant neutral loss scanning was used for substructure specific screening of THCCs in food samples. Detection limits for HPLC-ESI-MS/MS analysis of THCCs applying neutral loss experiments were established at 100 ng mL(-1) (ca. 2.5 pmol on column). Application of this MS/MS method enabled us to detect THCC derivatives derived from Pictet-Spengler condensation of tryptophan with alpha-oxo acids. Subsequently, diastereomeric 1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid 3a/b, 1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid 4a/b, and 1-(2'-carboxyethyl)-1,2,3,4-tetrahydro-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 5a/b were identified in alcoholic beverages, seasoning sauces, yeast extract, and fruit products for the first time. Most food samples under study contained 3a/b and 4a/b in significant amounts. 5a/b was identified in soy sauce, worcestershire sauce, seasoning sauce, and yeast extract. Due to the excellent selectivity of tandem mass spectrometry coeluting tetrahydro-beta-carboline derivatives could be identified unequivocally by HPLC-ESI-MS/MS.

  DOI：

  10.1021/jf960952h

文献信息

• HPLC−MS/MS Profiling of Tryptophan-Derived Alkaloids in Food:  Identification of Tetrahydro-β-carbolinedicarboxylic Acids
  作者：B. Gutsche、M. Herderich

  DOI：10.1021/jf960952h

  日期：1997.7.1

  A method for selective detection of 1,2,3,4-tetrahydro-beta-carbolinecarboxylic acids (THCCs) was developed based on electrospray ionization-tandem mass spectrometry coupled to liquid chromatography (HPLC-ESI-MS/MS). Low-energy collision-induced dissociation (CID) led to characteristic fragment ions due to neutral loss of 73 amu. Subsequently, constant neutral loss scanning was used for substructure specific screening of THCCs in food samples. Detection limits for HPLC-ESI-MS/MS analysis of THCCs applying neutral loss experiments were established at 100 ng mL(-1) (ca. 2.5 pmol on column). Application of this MS/MS method enabled us to detect THCC derivatives derived from Pictet-Spengler condensation of tryptophan with alpha-oxo acids. Subsequently, diastereomeric 1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid 3a/b, 1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid 4a/b, and 1-(2'-carboxyethyl)-1,2,3,4-tetrahydro-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 5a/b were identified in alcoholic beverages, seasoning sauces, yeast extract, and fruit products for the first time. Most food samples under study contained 3a/b and 4a/b in significant amounts. 5a/b was identified in soy sauce, worcestershire sauce, seasoning sauce, and yeast extract. Due to the excellent selectivity of tandem mass spectrometry coeluting tetrahydro-beta-carboline derivatives could be identified unequivocally by HPLC-ESI-MS/MS.