6-(2-甲酰基吡咯-1-基)己酸 | 61837-40-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 6-(2-甲酰基吡咯-1-基)己酸
• 英文名称: 6-(2-formyl-1-pyrrolyl)caproic acid
• 英文别名: 6-(2-Formyl-1H-pyrrol-1-yl)hexanoic acid；6-(2-formylpyrrol-1-yl)hexanoic acid
• CAS: 61837-40-9
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: HRXPOSKMHQHUME-UHFFFAOYSA-N

物化性质

• 沸点：
  399.8±22.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  fructopyranose 、 6-氨基己酸 在 phosphate buffer pH 7.0 作用下， 反应 2.0h， 生成 6-(2-甲酰基吡咯-1-基)己酸 、 6-(2-acetyl-1-pyrrolyl)caproic acid 、 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-3,4-dimethyl-2,5-dioxo-
  参考文献：
  名称：

  Structure and Potential Crosslinking Reactivity of a New Pentose-Specific Maillard Product

  摘要：

  The Maillard reaction of model compounds for peptide-bound lysine (4-aminobutyric acid, 6-aminocaproic acid, N-alpha-acetyl-L-lysine) with reducing sugars (D-ribose, D-xylose, D-arabinose, D-glucose, D-fructose, D-glyceraldehyde) was investigated under both stringent and mild conditions. With pentoses the corresponding omega-(dimethylmaleimido)carboxylic acids 1-3 were identified as substantial, hitherto unknown components by GC/MS and NMR. Their structure was confirmed by synthesis. A pathway to compounds 1-3 was derived from the results of 4-aminobutyric acid/[1-C-13]-D-arabinose isotopic labeling experiments. The new N-(dimethylmaleoyl)-omega-aminocarboxylic acid derivatives are shown to react under very mild conditions (pH 7, 32 degrees C) with thiols (methyl 3-mercaptopropionate, N-alpha-acetyl-L-cysteine methyl ester) to form the addition products 4-6. This reaction demonstrates that compounds of type 1-3 can be considered as potential protein cross-linkers in Maillard reactions.

  DOI：

  10.1021/jf00048a009

文献信息

• US3996940A
  申请人：——

  公开号：US3996940A

  公开（公告）日：1976-12-14
• Structure and Potential Crosslinking Reactivity of a New Pentose-Specific Maillard Product
  作者：Roland Tressl、Georg Wondrak、Evelyn Kersten、Dieter Rewicki

  DOI：10.1021/jf00048a009

  日期：1994.12

  The Maillard reaction of model compounds for peptide-bound lysine (4-aminobutyric acid, 6-aminocaproic acid, N-alpha-acetyl-L-lysine) with reducing sugars (D-ribose, D-xylose, D-arabinose, D-glucose, D-fructose, D-glyceraldehyde) was investigated under both stringent and mild conditions. With pentoses the corresponding omega-(dimethylmaleimido)carboxylic acids 1-3 were identified as substantial, hitherto unknown components by GC/MS and NMR. Their structure was confirmed by synthesis. A pathway to compounds 1-3 was derived from the results of 4-aminobutyric acid/[1-C-13]-D-arabinose isotopic labeling experiments. The new N-(dimethylmaleoyl)-omega-aminocarboxylic acid derivatives are shown to react under very mild conditions (pH 7, 32 degrees C) with thiols (methyl 3-mercaptopropionate, N-alpha-acetyl-L-cysteine methyl ester) to form the addition products 4-6. This reaction demonstrates that compounds of type 1-3 can be considered as potential protein cross-linkers in Maillard reactions.