2-(<13C>formyl-5-methyl-1-pyrrolyl)-3-methylpentanoic acid

• 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: 2-(<13C>formyl-5-methyl-1-pyrrolyl)-3-methylpentanoic acid
• 英文别名: 3-methyl-2-[2-methyl-5-(oxo(113C)methyl)pyrrol-1-yl]pentanoic acid
• 化学式: C₁₂H₁₇NO₃
• 分子量: 224.261
• InChiKey: AKAVJPALYOENKJ-CDYZYAPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-异亮氨酸 、 ¹³C-C1-glucopyranose 反应 1.5h， 生成 5-methyl-1H-pyrrole-2-carbaldehyde 、 2-(<13C>formyl-5-methyl-1-pyrrolyl)-3-methylpentanoic acid 、 2-<2-<(hydroxymethyl)carbonyl>-1-<5-13C>pyrrolyl>-3-methylpentanoic acid 、 2-<2-<(hydroxy<13C>-methyl)carbonyl>-1-pyrrolyl>-3-methylpentanoic acid 、 2-<2-<13C>formyl-5-(hydroxymethyl)-1-pyrrolyl>-3-methylpentanoic acid lactone 、 2-<2-<13C>formyl-5-(hydroxymethyl)-1-pyrrolyl>-3-methylpentanoic acid
  参考文献：
  名称：

  Formation of Isoleucine-Specific Maillard Products from [1-13C]-D-Glucose and [1-13C]-D-Fructose

  摘要：

  The Maillard reaction of 1-C-13-labeled D-glucose and D-fructose with L-isoleucine was investigated. The extent and position of the isotopic labeling (from MS data) were used to evaluate origin, reactive intermediates, and formation pathways of pyrroles and pyridinoles. The results are representative for primary alpha-amino acids. The observed distribution of the label supports 3-deoxyaldoketoses as intermediates of 2-formylpyrroles (1, 3, 7) and disqualifies 4-deoxy- and 1-deoxydiketose routes to 2-acetylpyrroles (2, 4, 9), respectively. Significant differences are observed in the formation of N-alkyl-2-acetylpyrroles and 2-acetylpyrrole in isoleucine (alpha-amino acid) and 4-aminobutyric acid (amine) Maillard experiments. Identically labeled pyrroles (1, 6, 7, 9) and pyridinoles (8, 10) from D-glucose and D-fructose confirm identical intermediates in the corresponding Maillard systems.

  DOI：

  10.1021/jf00053a009

文献信息

• Formation of Isoleucine-Specific Maillard Products from [1-13C]-D-Glucose and [1-13C]-D-Fructose
  作者：Roland Tressl、Christiane Nittka、Evelyn Kersten、Dieter Rewicki

  DOI：10.1021/jf00053a009

  日期：1995.5

  The Maillard reaction of 1-C-13-labeled D-glucose and D-fructose with L-isoleucine was investigated. The extent and position of the isotopic labeling (from MS data) were used to evaluate origin, reactive intermediates, and formation pathways of pyrroles and pyridinoles. The results are representative for primary alpha-amino acids. The observed distribution of the label supports 3-deoxyaldoketoses as intermediates of 2-formylpyrroles (1, 3, 7) and disqualifies 4-deoxy- and 1-deoxydiketose routes to 2-acetylpyrroles (2, 4, 9), respectively. Significant differences are observed in the formation of N-alkyl-2-acetylpyrroles and 2-acetylpyrrole in isoleucine (alpha-amino acid) and 4-aminobutyric acid (amine) Maillard experiments. Identically labeled pyrroles (1, 6, 7, 9) and pyridinoles (8, 10) from D-glucose and D-fructose confirm identical intermediates in the corresponding Maillard systems.