methyl 6-(3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrol-1-yl)hexanoate | 158905-53-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-(3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrol-1-yl)hexanoate
• 英文别名: Methyl 6-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)hexanoate；methyl 6-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)hexanoate
• CAS: 158905-53-4
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: JHKWZKIVONZHIC-UHFFFAOYSA-N

物化性质

• 沸点：
  357.7±25.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-半胱氨酸甲酯 、 methyl 6-(3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrol-1-yl)hexanoate 在 phosphate buffer pH 7 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以24%的产率得到methyl 6-<3,4-dimethyl-3-<<2-(methoxycarbonyl)-2-(acetylamino)ethyl>thio>-2,5-dioxopyrrolidin-1-yl>hexanoate
  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
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 在 sodium hydroxide 、 三氟化硼 作用下， 反应 2.67h， 生成 methyl 6-(3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrol-1-yl)hexanoate
  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

• 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.