N-<1-Desoxy-1-D-fructosyl>-ε-amino-capronsaeure | 15898-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-<1-Desoxy-1-D-fructosyl>-ε-amino-capronsaeure
• 英文别名: N(ε)-(1-deoxy-D-fructos-1-yl)-aminocaproic acid；6-[[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino]hexanoic acid
• CAS: 15898-19-8
• 化学式: C₁₂H₂₃NO₇
• 分子量: 293.317
• InChiKey: HORCTLJYNYMSOF-YUSALJHKSA-N

物化性质

• 沸点：
  617.9±55.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  147
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-<1-Desoxy-1-D-fructosyl>-ε-amino-capronsaeure 、 6-氨基己酸 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 360.0h， 生成 1,3-bis(5-carboxypentyl)-5-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-3-ium
  参考文献：
  名称：

  Favored and disfavored pathways of protein crosslinking by glucose: glucose lysine dimer (GLUCOLD) and crossline versus glucosepane

  摘要：

  We describe the isolation and molecular characterization of a novel glucose-lysine dimer crosslink 1,3-bis-(5-amino-5-carboxypentyl)-4-(1',2',3',4'-tetrahydroxybutyl)-3H-imidazolium salt, named GLUCOLD. GLUCOLD was easily formed from the Amadori product (fructose-lysine). However, when BSA was incubated with 100 mM glucose for 25 days, the levels of the lysine-lysine glucose crosslinks GLUCOLD and CROSSLINE were only 21 and < 1 pmol/mg, respectively, compared to 611 pmol/mg protein for the lysine-arginine GLUCOSEPANE crosslink, in spite of more than 20 potential lysine-lysine crosslinking sites in the protein. Mechanistic investigation revealed that metal-free phosphate ions catalyzed formation of fructose-lysine and all three crosslinks from amino acids, while cationic MOPS buffer had an opposite effect. This together with the rapid formation of N (6)-1,4-dideoxy-5,6-dioxoglucosone derivatives by dicarbonyl trapping agents, such as 1,2-diaminobenzene or gamma-guanidinobutyric acid, strongly suggests that enolization of the Amadori product and trapping of the 5,6-dioxo derivative by arginine residues constitutes the major pathway for glucose-mediated crosslinking in proteins.

  DOI：

  10.1007/s00726-010-0631-2
• 作为产物：
  描述：

  葡萄糖 、 6-氨基己酸 以 甲醇 为溶剂， 生成 N-<1-Desoxy-1-D-fructosyl>-ε-amino-capronsaeure
  参考文献：
  名称：

  Berrens,L., Recueil des Travaux Chimiques des Pays-Bas, 1966, vol. 85, p. 1117 - 1128

  摘要：

  DOI：