2-formyl-3-(hexylamino)butanal | 220405-04-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-formyl-3-(hexylamino)butanal
• 英文别名: 2-[1-(Hexylamino)ethyl]propanedial
• CAS: 220405-04-9
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: USBNBCYEFOJMRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-ethylaminopropenal 、 2-formyl-3-(hexylamino)butanal 以 phosphate buffer 为溶剂， 生成 1-ethyl-4-methyl-1,4-dihydro-3,5-pyridinedicarboxaldehyde
  参考文献：
  名称：

  Elucidation of Reaction Scheme Describing Malondialdehyde−Acetaldehyde−Protein Adduct Formation

  摘要：

  Malondialdehyde and acetaldehyde react together with proteins and form hybrid protein conjugates designated as MAA adducts, which have been detected in livers of ethanol-fed animals. Our previous studies have shown that MAA adducts are comprised of two distinct products. One adduct is composed of two molecules of malondialdehyde and one molecule of acetaldehyde and was identified as the 4-methpl-1,4-dihydropyridine-3,5-dicarbaldehyde derivative of an amino group (MHHDC adduct). The other adduct is a 1:1 adduct of malondialdehyde and acetaldehyde and was identified as the 2-formyl-3-(alkylamino)butanal derivative of an amino group (FAAB adduct). In this study, information on the mechanism of MAA adduct formation was obtained, focusing on whether the FAAB adduct serves as a precursor for the MDHDC adduct. Upon the basis of chemical analysis and NMR spectroscopy, two initial reaction steps appear to be a prerequisite for MDHDC formation. One step involves the reaction of one molecule of malondialdehyde and one of acetaldehyde with an amino group of a protein to form the FAAB product, while the other step involves the generation of a malondialdehyde-enamine. It appears that generation of the MDHDC adduct requires the FAAB moiety to be transferred to the nitrogen of the MDA-enamine. For efficient reaction of FAAB with the enamine to take place, additional experiments indicated that these two intermediates likely must be in positions on the protein of close proximity to each other. Further studies showed that the incubation of liver proteins from ethanol-fed rats with MDA resulted in a marked generation of MDHDC adducts, indicating the presence of a pool of FAAB adducts in the liver of ethanol-fed animals. Overall, these findings show that MDHDC-protein adduct formation occurs via the reaction of the FAAB moiety with a malondialdehyde-enamine, and further suggest that a similar mechanism may be operative in vivo in the liver during prolonged ethanol consumption.

  DOI：

  10.1021/tx000222a
• 作为产物：
  描述：

  丙二醛 、 正己胺 、 乙醛 以 水 为溶剂， 反应 1.0h， 以13%的产率得到2-formyl-3-(hexylamino)butanal
  参考文献：
  名称：

  通过13 C NMR光谱观察新的非荧光丙二醛-乙醛-蛋白质加合物。

  摘要：

  已经显示丙二醛（MDA）和乙醛通过赖氨酸残基的ε-氨基与蛋白质反应，产生杂合的MDA-乙醛（MAA）-蛋白质加合物。一种MAA加合物的结构已确认为4-甲基-1，4-二氢吡啶-3,5-二甲醛（3）。在这项研究中，使用13 C NMR光谱鉴定第二个MAA加合物的结构为2-甲酰基-3-（烷基氨基）丁醛（4）。在各种条件下，将同位素标记的[1-13C]乙醛与MDA和蛋白质（牛血清白蛋白）反应，并通过13C NMR在不同的时间间隔监控反应。在每个实验中，新信号分别以50 ppm和22 ppm的速度增长。与模型化合物比较，在50 ppm处的信号对应于2-甲酰基-3-（烷基氨基）丁醛加合物，在22 ppm处的信号对应于已知的1，4-二氢吡啶-3，5-二甲醛加合物。当BSA被多聚赖氨酸替代时，发现了相似的结果。总体而言，MAA蛋白加合物似乎由两个主要产物3和4组成。

  DOI：

  10.1021/tx980132u